Synthesis of acetaldehyde diethyl acetal

Preparation of acetaldehyde diethyl acetal (acetal; diethyl acetal; ethane, 1,1-diethoxy-)

Preparation of acetaldehyde diethyl acetal (Acetal; diethyl acetal; ethane, 1,1-diethoxy-)

Preparation of acetaldehyde diethyl acetal (Acetal; diethyl acetal; ethane, 1,1-diethoxy-)

50 g of anhydrous calcium chloride and 323 ml (260 g) of 95% ethyl alcohol are placed in a 1-liter narrow neck flask, which is cooled to 8° or below by immersion in ice water. Slowly 155 ml (125 g) of freshly distilled acetaldehyde (b.p. 20-22° C) are added down the sides of the flask so that it forms a layer on the alcoholic solution. The flask is tightly stoppered and shaken vigorously for 3-4 minutes and a considerable rise in temperature occurs so that the stopper must be held well down to prevent the volatilization of the acetaldehyde. The stoppered flask is left to stand for 24-36 hours with intermittent shaking, whereupon standing after 1-2 hours the mixture separates into two layers. The upper layer is separated (320 g.) and washed three times with 80 ml portions of water, then dried for several hours over anhydrous potassium carbonate and purified by fractionating with an efficient column. The fraction boiling at 101-104° C is collected yielding 200 g of pure acetaldehyde diethyl acetal.

A text book of practical organic chemistry, by A. I. Vogel, 327, 1974

IUPAC Name

1,1-diethoxyethane

InChI

InChI=1S/C6H14O2/c1-4-7-6(3)8-5-2/h6H,4-5H2,1-3H3

InChI Key

DHKHKXVYLBGOIT-UHFFFAOYSA-N

Canonical SMILES

CCOC(C)OCC

MeSH Synonyms

polyacetal

Depositor-Supplied Synonyms

Acetal, 1,1-DIETHOXYETHANE, Diethyl acetal, 105-57-7, Ethane, 1,1-diethoxy-, Acetaldehyde diethyl acetal, Ethylidene diethyl ether, Diaethylacetal, Acetaldehyde, diethyl acetal, Acetal diethylique, 1,1-Dietossietano, 1,1-Diethoxy-ethaan, diethoxyethane, 1,1-Diaethoxy-aethan, Diethylacetal, Acetaal, Acetale, Acetaal [Dutch], Acetal (natural), USAF DO-45, Acetale [Italian], Ethylidenediethyl ether, Diaethylacetal [German], Acetaldehyde ethyl acetal, NSC 7624, Acetal diethylique [French], UNII-5G14F9E2HB, 1,1-Dietossietano [Italian], FEMA No. 2002, 1,1-Diethoxy-ethaan [Dutch], 1,1-Diaethoxy-aethan [German], HSDB 1635, DHKHKXVYLBGOIT-UHFFFAOYSA-N, EINECS 203-310-6, UN1088, BRN 1098310, NCGC00091076-01, AI3-24135, DSSTox_CID_10607, DSSTox_RID_78853, DSSTox_GSID_30607, CAS-105-57-7, polyacetal, Capsicum annuum l, Ethane, diethoxy-, Ethane, 1,1-diethoxy-, homopolymer, 1,1-diethoxy-ethane, Ethanal diethyl acetal, Diethoxy-1,1-ethane, Ethylidine diethyl ether, AC1L1PHX, A902_ALDRICH, AC1Q35EI, SCHEMBL9459, KSC175C2F, CH3CH(OC2H5)2, W200204_ALDRICH, W200220_ALDRICH, 5G14F9E2HB, AC1Q2C35, CHEMBL1338583, 00109_FLUKA, CTK0H5122, C6H14O2, NSC7624, WLN: 2OY1 & O2, MolPort-001-779-696, BB_SC-7086, NSC-7624, Tox21_111078, Tox21_200274, Acetal (Acetaldehyde diethyl acetal), AR-1H6101, BBL011492, SBB058503, STL146604, ZINC00404268, AKOS005721110, Acetal [UN1088] [Flammable liquid], AN-1413, LS-2076, MCULE-7152410134, NE10641, RL00250, UN 1088, Acetal [UN1088] [Flammable liquid], NCGC00091076-02, NCGC00257828-01, 30846-29-8, CJ-03987, KB-47039, ZB013439, TR-001161, D0455, ST51023417, EN300-20127, 23275-EP2314584A1, 119041-EP2277880A1, 119041-EP2292610A1, 119041-EP2298756A1, S14-1489, 3B3-020235, InChI=1/C6H14O2/c1-4-7-6(3)8-5-2/h6H,4-5H2,1-3H, 73506-93-1

Removed Synonyms

Acetol, Ethane,1-diethoxy-, CID7765, 4-01-00-03103 (Beilstein Handbook Reference), 106061-05-6

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