Synthesis of ethyl acetate

Preparation of ethyl acetate

Preparation of ethyl acetate

Preparation of ethyl acetate

A 500 ml round bottom flask, containing a mixture of 50 ml of ethyl alcohol and 50 ml of concentrated sulfuric acid, is fitted with dropping funnel and distillation head with condenser. The reaction flask is heated and when the temperature reaches 140° C  a mixture of 400 ml of ethyl alcohol and 400 ml of glacial acetic acid is gradually added through the funnel, at the same rate at which the ethyl acetate, formed in the reaction, distills over. In order to remove the glacial acetic acid carried over, the distillate is neutralized with a dilute solution of sodium carbonate. The organic upper layer is separated with a separatory funnel, filtered, and in order to remove the alcohol is treated with a solution of 100 g of calcium chloride in 100 ml of water. Organic (upper) layer is again separated, dried with calcium chloride and then distilled collecting fraction boiling at 78° C. Yield of ethyl acetate is about 80-90%.

The practical methods of organic chemistry, by L. Gattermann, 137-138, 1909

Preparation of ethyl acetate

Preparation of ethyl acetate

To 10 g of absolute alcohol, 15 g of acetyl chloride are added drop by drop with good cooling and shaking, the temporatttre not being allowed to rise above 20° C. The whole is carefully diluted with an equal volume of saturated brine, and the ethyl acetate which floats on the surface separated, well washed with a 50% solution of calcium chloride to remove alcohol, dried for 24 hours over calcium chloride, and fractionated, the fraction 74-81° C being redistilled. Yield almost theoretical.

Systematic organic chemistry, by W. M. Cumming, 260-261, 1937.

IUPAC Name

ethyl acetate

InChI

InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3

InChI Key

XEKOWRVHYACXOJ-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)C

MeSH Synonyms

ethyl acetate

Depositor-Supplied Synonyms

ETHYL ACETATE, Ethyl ethanoate, Acetoxyethane, Vinegar naphtha, Ethyl acetic ester, Acetic ether, 141-78-6, Acetic acid ethyl ester, Acetic acid, ethyl ester, Essigester, Acetidin, Acetic ester, Ethylacetate, AcOEt, Aethylacetat, RCRA waste number U112, Ethyl ester, 1-acetoxyethane, EtOAc, Ethylacetaat, Ethylazetat, Octan etylu, Essigsaeureethylester, Etile (acetato di), Essigester [German], Ethylacetaat [Dutch], Aethylacetat [German], Caswell No. 429, CHEBI:27750, Ethyle (acetate d’), Octan etylu [Polish], Ethyl acetate (natural), Ethylester kyseliny octove, NSC 70930, CH3COOC2H5, Acetate d’ethyle [French], RCRA waste no. U112, Acetato de etilo [Spanish], CH3-CO-O-CH3, HSDB 83, ethyl acetat, UNII-76845O8NMZ, FEMA No. 2414, CCRIS 6036, Etile (acetato di) [Italian], Ethyle (acetate d’) [French], XEKOWRVHYACXOJ-UHFFFAOYSA-N, Ethylester kyseliny octove [Czech], EINECS 205-500-4, UN1173, Ethyl acetate (NF), Ethyl acetate [NF], EPA Pesticide Chemical Code 044003, NCGC00091766-01, AI3-00404, DSSTox_CID_2001, DSSTox_RID_76453, DSSTox_GSID_22001, CAS-141-78-6, EEE, acet-ethylester, ehtyl acetate, ethyl-acetate, Acetyl ester, acet-eth-ester, Acetate d’ethyle, Acetato de etilo, acetic ethyl ester, Etile(acetato di), Ethyle(acetate d’), acetic acid ethylester, acetic-acid-ethylester, ACMC-1BTXP, Ethyl acetate, 99.9%, ETHYL ACETATE, ACS, Epitope ID:116868, Ethyl ester of acetic acid, AC1L1RU4, AC1Q35EC, KSC492C3D, WLN: 2OV1, CHEMBL14152, W241407_ALDRICH, W241415_ALDRICH, ACETIC ACID,ETHYL ESTER, 270989_ALDRICH, 27227_RIEDEL, 320307_ALDRICH, 33211_RIEDEL, 34490_RIEDEL, 34972_RIEDEL, 414743_ALDRICH, 442583_SUPELCO, 494518_ALDRICH, 537446_ALDRICH, 650528_ALDRICH, 09652_FLUKA, 34490_FLUKA, 34972_FLUKA, 45765_FLUKA, 45767_FLUKA, 58958_FLUKA, CTK3J2131, MolPort-000-871-940, 27227_SIAL, 33211_SIAL, 34858_SIAL, 45767_SIAL, 76845O8NMZ, LTBB002232, 154857_SIAL, 270989_SIAL, 319902_SIAL, 320307_SIAL, 494518_SIAL, 537446_SIAL, 650528_SIAL, 676810_SIAL, NSC70930, Tox21_111166, Tox21_202512, ANW-42221, c0036, LS-831, NSC-70930, STL282717, ZINC00895412, AKOS000121947, MCULE-6628539781, RL01740, RTR-005372, UN 1173, NCGC00260061-01, AN-23212, KB-51510, ZB015033, TR-005372, 936-EP0930075A1, 936-EP1441224A2, 936-EP2269610A2, 936-EP2269651A2, 936-EP2269975A2, 936-EP2269977A2, 936-EP2269986A1, 936-EP2269987A1, 936-EP2269988A2, 936-EP2269989A1, 936-EP2269990A1, 936-EP2269992A1, 936-EP2269993A1, 936-EP2269994A1, 936-EP2269997A2, 936-EP2270000A1, 936-EP2270003A1, 936-EP2270004A1, 936-EP2270006A1, 936-EP2270008A1, 936-EP2270009A1, 936-EP2270011A1, 936-EP2270014A1, 936-EP2270015A1, 936-EP2270113A1, 936-EP2270114A1, 936-EP2272509A1, 936-EP2272516A2, 936-EP2272517A1, 936-EP2272537A2, 936-EP2272813A2, 936-EP2272817A1, 936-EP2272822A1, 936-EP2272825A2, 936-EP2272827A1, 936-EP2272829A2, 936-EP2272830A1, 936-EP2272832A1, 936-EP2272834A1, 936-EP2272835A1, 936-EP2272839A1, 936-EP2272840A1, 936-EP2272841A1, 936-EP2272842A1, 936-EP2272843A1, 936-EP2272844A1, 936-EP2272847A1, 936-EP2272848A1, 936-EP2272849A1, 936-EP2272935A1, 936-EP2272972A1, 936-EP2272973A1, 936-EP2274983A1, 936-EP2275102A1, 936-EP2275105A1, 936-EP2275395A2, 936-EP2275398A1, 936-EP2275401A1, 936-EP2275403A1, 936-EP2275404A1, 936-EP2275407A1, 936-EP2275410A1, 936-EP2275411A2, 936-EP2275412A1, 936-EP2275413A1, 936-EP2275414A1, 936-EP2275415A2, 936-EP2275419A2, 936-EP2275420A1, 936-EP2275421A1, 936-EP2275423A1, 936-EP2275469A1, 936-EP2277565A2, 936-EP2277566A2, 936-EP2277567A1, 936-EP2277568A2, 936-EP2277569A2, 936-EP2277570A2, 936-EP2277858A1, 936-EP2277861A1, 936-EP2277865A1, 936-EP2277866A1, 936-EP2277867A2, 936-EP2277872A1, 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936-EP2287147A2, 936-EP2287152A2, 936-EP2287153A1, 936-EP2287154A1, 936-EP2287155A1, 936-EP2287156A1, 936-EP2287160A1, 936-EP2287161A1, 936-EP2287162A1, 936-EP2287165A2, 936-EP2287166A2, 936-EP2287167A1, 936-EP2287168A2, 936-EP2287940A1, 936-EP2289509A2, 936-EP2289510A1, 936-EP2289868A1, 936-EP2289871A1, 936-EP2289876A1, 936-EP2289877A1, 936-EP2289878A1, 936-EP2289879A1, 936-EP2289883A1, 936-EP2289884A1, 936-EP2289885A1, 936-EP2289887A2, 936-EP2289888A2, 936-EP2289890A1, 936-EP2289892A1, 936-EP2289893A1, 936-EP2289894A2, 936-EP2289965A1, 936-EP2292088A1, 936-EP2292227A2, 936-EP2292228A1, 936-EP2292234A1, 936-EP2292280A1, 936-EP2292576A2, 936-EP2292586A2, 936-EP2292589A1, 936-EP2292592A1, 936-EP2292593A2, 936-EP2292595A1, 936-EP2292596A2, 936-EP2292597A1, 936-EP2292599A1, 936-EP2292606A1, 936-EP2292607A2, 936-EP2292609A1, 936-EP2292610A1, 936-EP2292611A1, 936-EP2292612A2, 936-EP2292613A1, 936-EP2292614A1, 936-EP2292615A1, 936-EP2292617A1, 936-EP2292619A1, 936-EP2292620A2, 936-EP2292621A1, 936-EP2292622A1, 936-EP2292624A1, 936-EP2292628A2, 936-EP2292630A1, 936-EP2295055A2, 936-EP2295401A2, 936-EP2295402A2, 936-EP2295406A1, 936-EP2295407A1, 936-EP2295408A1, 936-EP2295409A1, 936-EP2295411A1, 936-EP2295412A1, 936-EP2295413A1, 936-EP2295414A1, 936-EP2295415A1, 936-EP2295416A2, 936-EP2295417A1, 936-EP2295418A1, 936-EP2295423A1, 936-EP2295424A1, 936-EP2295425A1, 936-EP2295426A1, 936-EP2295427A1, 936-EP2295429A1, 936-EP2295430A2, 936-EP2295431A2, 936-EP2295432A1, 936-EP2295433A2, 936-EP2295434A2, 936-EP2295435A1, 936-EP2295437A1, 936-EP2295438A1, 936-EP2295439A1, 936-EP2295441A2, 936-EP2295503A1, 936-EP2298312A1, 936-EP2298313A1, 936-EP2298729A1, 936-EP2298731A1, 936-EP2298734A2, 936-EP2298735A1, 936-EP2298736A1, 936-EP2298738A1, 936-EP2298742A1, 936-EP2298743A1, 936-EP2298744A2, 936-EP2298745A1, 936-EP2298746A1, 936-EP2298747A1, 936-EP2298748A2, 936-EP2298750A1, 936-EP2298751A2, 936-EP2298752A1, 936-EP2298753A1, 936-EP2298754A1, 936-EP2298755A1, 936-EP2298756A1, 936-EP2298757A2, 936-EP2298758A1, 936-EP2298759A1, 936-EP2298761A1, 936-EP2298763A1, 936-EP2298764A1, 936-EP2298765A1, 936-EP2298766A1, 936-EP2298767A1, 936-EP2298768A1, 936-EP2298770A1, 936-EP2298772A1, 936-EP2298774A1, 936-EP2298775A1, 936-EP2298776A1, 936-EP2298777A2, 936-EP2298778A1, 936-EP2298779A1, 936-EP2298828A1, 936-EP2299326A1, 936-EP2299510A1, 936-EP2301533A1, 936-EP2301536A1, 936-EP2301538A1, 936-EP2301627A1, 936-EP2301909A1, 936-EP2301911A1, 936-EP2301918A1, 936-EP2301921A1, 936-EP2301922A1, 936-EP2301923A1, 936-EP2301924A1, 936-EP2301925A1, 936-EP2301926A1, 936-EP2301928A1, 936-EP2301929A1, 936-EP2301930A1, 936-EP2301931A1, 936-EP2301932A1, 936-EP2301933A1, 936-EP2301934A1, 936-EP2301935A1, 936-EP2301936A1, 936-EP2301937A1, 936-EP2301938A1, 936-EP2301939A1, 936-EP2301940A1, 936-EP2301983A1, 936-EP2302003A1, 936-EP2302382A2, 936-EP2302383A2, 936-EP2305243A1, 936-EP2305248A1, 936-EP2305250A1, 936-EP2305254A1, 936-EP2305625A1, 936-EP2305627A1, 936-EP2305629A1, 936-EP2305633A1, 936-EP2305636A1, 936-EP2305640A2, 936-EP2305641A1, 936-EP2305642A2, 936-EP2305643A1, 936-EP2305644A1, 936-EP2305646A1, 936-EP2305647A1, 936-EP2305648A1, 936-EP2305649A1, 936-EP2305650A1, 936-EP2305651A1, 936-EP2305652A2, 936-EP2305655A2, 936-EP2305657A2, 936-EP2305658A1, 936-EP2305659A1, 936-EP2305660A1, 936-EP2305663A1, 936-EP2305664A1, 936-EP2305666A1, 936-EP2305667A2, 936-EP2305668A1, 936-EP2305669A1, 936-EP2305670A1, 936-EP2305671A1, 936-EP2305672A1, 936-EP2305673A1, 936-EP2305674A1, 936-EP2305675A1, 936-EP2305676A1, 936-EP2305677A1, 936-EP2305680A2, 936-EP2305682A1, 936-EP2305683A1, 936-EP2305684A1, 936-EP2305685A1, 936-EP2305686A1, 936-EP2305687A1, 936-EP2305688A1, 936-EP2305689A1, 936-EP2305695A2, 936-EP2305696A2, 936-EP2305697A2, 936-EP2305698A2, 936-EP2305769A2, 936-EP2305808A1, 936-EP2305825A1, 936-EP2308471A1, 936-EP2308479A2, 936-EP2308510A1, 936-EP2308562A2, 936-EP2308812A2, 936-EP2308828A2, 936-EP2308832A1, 936-EP2308833A2, 936-EP2308838A1, 936-EP2308839A1, 936-EP2308841A2, 936-EP2308842A1, 936-EP2308843A1, 936-EP2308844A2, 936-EP2308845A2, 936-EP2308846A2, 936-EP2308847A1, 936-EP2308848A1, 936-EP2308849A1, 936-EP2308850A1, 936-EP2308851A1, 936-EP2308853A1, 936-EP2308854A1, 936-EP2308855A1, 936-EP2308857A1, 936-EP2308858A1, 936-EP2308861A1, 936-EP2308862A1, 936-EP2308864A1, 936-EP2308865A1, 936-EP2308867A2, 936-EP2308868A1, 936-EP2308869A1, 936-EP2308870A2, 936-EP2308871A1, 936-EP2308872A1, 936-EP2308873A1, 936-EP2308874A1, 936-EP2308875A1, 936-EP2308876A1, 936-EP2308877A1, 936-EP2308879A1, 936-EP2308880A1, 936-EP2308882A1, 936-EP2308926A1, 936-EP2308960A1, 936-EP2309564A1, 936-EP2309584A1, 936-EP2311453A1, 936-EP2311455A1, 936-EP2311464A1, 936-EP2311494A1, 936-EP2311796A1, 936-EP2311797A1, 936-EP2311798A1, 936-EP2311799A1, 936-EP2311801A1, 936-EP2311802A1, 936-EP2311803A1, 936-EP2311805A1, 936-EP2311806A2, 936-EP2311807A1, 936-EP2311808A1, 936-EP2311809A1, 936-EP2311810A1, 936-EP2311811A1, 936-EP2311812A1, 936-EP2311813A1, 936-EP2311814A1, 936-EP2311815A1, 936-EP2311816A1, 936-EP2311817A1, 936-EP2311818A1, 936-EP2311820A1, 936-EP2311821A1, 936-EP2311822A1, 936-EP2311823A1, 936-EP2311824A1, 936-EP2311825A1, 936-EP2311827A1, 936-EP2311828A1, 936-EP2311829A1, 936-EP2311830A1, 936-EP2311831A1, 936-EP2311832A1, 936-EP2311833A1, 936-EP2311834A1, 936-EP2311836A1, 936-EP2311837A1, 936-EP2311839A1, 936-EP2311840A1, 936-EP2311841A1, 936-EP2311842A2, 936-EP2311850A1, 936-EP2314295A1, 936-EP2314558A1, 936-EP2314571A2, 936-EP2314574A1, 936-EP2314575A1, 936-EP2314576A1, 936-EP2314577A1, 936-EP2314579A1, 936-EP2314581A1, 936-EP2314582A1, 936-EP2314583A1, 936-EP2314584A1, 936-EP2314585A1, 936-EP2314586A1, 936-EP2314587A1, 936-EP2314588A1, 936-EP2314589A1, 936-EP2314590A1, 936-EP2314593A1, 936-EP2315303A1, 936-EP2315502A1, 936-EP2316452A1, 936-EP2316457A1, 936-EP2316458A1, 936-EP2316470A2, 936-EP2316824A1, 936-EP2316825A1, 936-EP2316826A1, 936-EP2316827A1, 936-EP2316828A1, 936-EP2316829A1, 936-EP2316831A1, 936-EP2316832A1, 936-EP2316833A1, 936-EP2316834A1, 936-EP2316835A1, 936-EP2316836A1, 936-EP2316837A1, 936-EP2316905A1, 936-EP2316906A2, 936-EP2316937A1, 936-EP2316974A1, 936-EP2371808A1, 936-EP2371810A1, 936-EP2371811A2, 936-EP2371813A1, 936-EP2371814A1, 936-EP2371831A1, 936-EP2374454A1, 936-EP2374538A1, 936-EP2374788A1, 936-EP2374790A1, 936-EP2377845A1, 936-EP2377847A1, 936-EP2380568A1, 936-EP2380661A2, 936-EP2380867A1, 936-EP2380873A1, 936-EP2380874A2, 949-EP2269996A1, 949-EP2270003A1, 949-EP2270008A1, 949-EP2270009A1, 949-EP2272830A1, 949-EP2275413A1, 949-EP2275421A1, 949-EP2281820A2, 949-EP2281822A1, 949-EP2284174A1, 949-EP2287156A1, 949-EP2287157A1, 949-EP2287159A1, 949-EP2292617A1, 949-EP2295428A2, 949-EP2295433A2, 949-EP2295441A2, 949-EP2298735A1, 949-EP2298754A1, 949-EP2298762A2, 949-EP2298774A1, 949-EP2298783A1, 949-EP2301921A1, 949-EP2301926A1, 949-EP2301932A1, 949-EP2301940A1, 949-EP2305646A1, 949-EP2305695A2, 949-EP2305696A2, 949-EP2305697A2, 949-EP2305698A2, 949-EP2308845A2, 949-EP2308846A2, 949-EP2308851A1, 949-EP2308861A1, 949-EP2308867A2, 949-EP2308870A2, 949-EP2308876A1, 949-EP2311494A1, 949-EP2311840A1, 949-EP2311841A1, 949-EP2314576A1, 949-EP2316824A1, 949-EP2316832A1, 949-EP2316833A1, 949-EP2380871A1, A0030, E1504, Ethyl acetate [UN1173] [Flammable liquid], FT-0621744, FT-0693343, Q0040, Q0044, Ethyl acetate [UN1173] [Flammable liquid], 6822-EP1441224A2, C00849, D02319, 37556-EP2305808A1, 37556-EP2311802A1, 37556-EP2311803A1, 300085X, A807811, 3B4-0103, I14-2577, InChI=1/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H, UNII-LM8ZO3J16V component XEKOWRVHYACXOJ-UHFFFAOYSA-N

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