Synthesis of tert-butyl alcohol (tert-butanol)

Preparation of tert-butyl alcohol

6 g of clean magnesium ribbon or filings are placed in a 1 liter dry, round flask connected with a long reflux condenser and dropping funnel. A mixture of 36 g of methyl iodide and 50 ml of ether, previously well dried over sodium is prepared and 20 ml of this mixture poured on to the magnesium. In a few seconds a vigorous reaction usually sets in or, if it is delayed, may be started by adding a crystal of iodine. When the first reaction has subsided, 70 ml of dry ether added and run in the remainder of the methyl iodide and ether mixture drop by drop from a dropping funnel. The reaction mixture is then boiled for a short time until the magnesium is dissolved. When all magnesium is dissolved the reaction flask is cooled to room temperature and then cooled with freezing mixture of powdered ice and sodium chloride. 12 g of acetone are added drop by drop forming an energetic reaction. Each drop of acetone produces a hissing sound and forms a white precipitate. After the acetone has been added, the mixture is left for a few hours, and carefully decomposed in the cold by the gradual addition of dilute sulfuric acid. The ethereal solution is removed and the aqueous portion distilled in steam to remove dissolved alcohol until about 100 ml have distilled. The distillate is saturated with potassium carbonate, extracted with ether and the ether solution added to the previous portion. The ether solution is dried over solid potassium carbonate and fractionated slowly at 40° C. The residue, which is tert-butyl alcohol containing water, is refluxed with 4 g of barium oxide for an hour and then distilled at 100° C yielding crude tert-butyl alcohol. Further purification is performed by refractionating crude tert-butyl alcohol and collected fraction passing at 81-83° C yield 8-10 g of final product.

A Class-Book of Organic Chemistry, by J. B. Cohen, 11-12, 1919

IUPAC Name

2-methylpropan-2-ol

InChI

InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3

InChI Key

DKGAVHZHDRPRBM-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)O

MeSH Synonyms

Alcohol, tert-Butyl, Alcohol, tertiary-Butyl, t Butanol, t-Butanol, tert Butanol, tert Butyl Alcohol, tert-Butanol, tert-Butyl Alcohol, tertiary Butyl Alcohol, tertiary-Butyl Alcohol

Depositor-Supplied Synonyms

tert-Butanol, tert-Butyl alcohol, 2-Methyl-2-propanol, 2-Methylpropan-2-ol, Trimethylcarbinol, t-Butanol, 75-65-0, 1,1-Dimethylethanol, t-Butyl hydroxide, 2-Propanol, 2-methyl-, Trimethyl methanol, Tertiary-Butyl Alcohol, tert-butylalcohol, Butanol tertiaire, T-BUTYL ALCOHOL, Trimethyl carbinol, Dimethylethanol, tertiary-Butanol, Trimethylmethanol, Alcool butylique tertiaire, Methanol, trimethyl-, Arconol, t-butylalcohol, tert.-butanol, tBuOH, Methyl-2-propanol, t-BuOH, Caswell No. 124A, NCI-C55367, Butanol tertiaire [French], UNII-MD83SFE959, HSDB 50, CCRIS 4755, CHEBI:45895, DKGAVHZHDRPRBM-UHFFFAOYSA-N, Alcool butylique tertiaire [French], EINECS 200-889-7, BRN 0906698, AI3-01288, tert Butanol, tert Butyl Alcohol, TBU, tertiary Butyl Alcohol, tertbutanol, tertiarybutanol, tert.butanol, t-butyl-alcohol, tertiary alcohol, tertiary butanol, tert -butanol, tertbutyl alcohol, tertiary alcohols, tert. Butanol, t- butanol, tert-butyl-alcohol, tert.-butylalcohol, tert.butyl alcohol, 2methyl-2-propanol, tert- butyl alcohol, tert. butyl alcohol, tert-Butyl hydroxide, Tert.-butyl alcohol, 2-Methylpropanol-2, tert-C4H9OH, 2-methyl,2-propanol, PubChem3012, Methyl-2 propanol-2, 1,1-dimethyl ethanol, 2-methyl-propan-2-ol, ACMC-209ozd, tert-Butanol; >99%, AC1L1MEX, 2-Methyl n-propan-2-ol, Ethanol, 1,1-Dimethyl-, AC1Q1MP2, AC1Q1MP3, KSC377O4L, CHEMBL16502, Tertiary butyl alcohol reagent, 308250_ALDRICH, 33067_RIEDEL, 442790_SUPELCO, 471712_ALDRICH, MD83SFE959, 19460_FLUKA, 50621_FLUKA, B85927_SIAL, CHEBI:26878, CTK2H7745, MolPort-001-783-135, 19460_SIAL, 33067_SIAL, LS-41, LTBB001498, 308250_SIAL, 360538_SIAL, 471712_SIAL, ANW-36647, STL282741, ZINC01680021, AKOS009029221, DB03900, MCULE-2451492095, RP18336, RTR-037684, AN-23865, BP-20656, CJ-06255, CJ-27536, KB-61358, TR-037684, B0706, FT-0688093, 6136-EP0930075A1, 6136-EP2270014A1, 6136-EP2274983A1, 6136-EP2286811A1, 6136-EP2287152A2, 6136-EP2289868A1, 6136-EP2292606A1, 6136-EP2295414A1, 6136-EP2295415A1, 6136-EP2298772A1, 6136-EP2305642A2, 6136-EP2305673A1, 6136-EP2308839A1, 6136-EP2311834A1, 6136-EP2374780A1, 6136-EP2374783A1, 6136-EP2377841A1, 6136-EP2380568A1, 10394-EP2269989A1, 10394-EP2269993A1, 10394-EP2270001A1, 10394-EP2270008A1, 10394-EP2270009A1, 10394-EP2270012A1, 10394-EP2270013A1, 10394-EP2272817A1, 10394-EP2272826A1, 10394-EP2275401A1, 10394-EP2275404A1, 10394-EP2277507A1, 10394-EP2277865A1, 10394-EP2284159A1, 10394-EP2284165A1, 10394-EP2286795A1, 10394-EP2287153A1, 10394-EP2287154A1, 10394-EP2287155A1, 10394-EP2287165A2, 10394-EP2287166A2, 10394-EP2289509A2, 10394-EP2289868A1, 10394-EP2289892A1, 10394-EP2292608A1, 10394-EP2292612A2, 10394-EP2292617A1, 10394-EP2292620A2, 10394-EP2295406A1, 10394-EP2295412A1, 10394-EP2295413A1, 10394-EP2295414A1, 10394-EP2295432A1, 10394-EP2298313A1, 10394-EP2298753A1, 10394-EP2298768A1, 10394-EP2301536A1, 10394-EP2301538A1, 10394-EP2301933A1, 10394-EP2305625A1, 10394-EP2305651A1, 10394-EP2305659A1, 10394-EP2305660A1, 10394-EP2305666A1, 10394-EP2305676A1, 10394-EP2305681A1, 10394-EP2308812A2, 10394-EP2308828A2, 10394-EP2308839A1, 10394-EP2308840A1, 10394-EP2308848A1, 10394-EP2308849A1, 10394-EP2308850A1, 10394-EP2308854A1, 10394-EP2308866A1, 10394-EP2308867A2, 10394-EP2308869A1, 10394-EP2308870A2, 10394-EP2308877A1, 10394-EP2311455A1, 10394-EP2311808A1, 10394-EP2311827A1, 10394-EP2311829A1, 10394-EP2311830A1, 10394-EP2311838A1, 10394-EP2314577A1, 10394-EP2314590A1, 10394-EP2315303A1, 10394-EP2316452A1, 10394-EP2377841A1, 10394-EP2380873A1, 15232-EP2272849A1, 15232-EP2275411A2, 15232-EP2275414A1, 15232-EP2277876A1, 15232-EP2280005A1, 15232-EP2281899A2, 15232-EP2284158A1, 15232-EP2284174A1, 15232-EP2286811A1, 15232-EP2289868A1, 15232-EP2289884A1, 15232-EP2292589A1, 15232-EP2292607A2, 15232-EP2292613A1, 15232-EP2292614A1, 15232-EP2292619A1, 15232-EP2292622A1, 15232-EP2295415A1, 15232-EP2295422A2, 15232-EP2298729A1, 15232-EP2298742A1, 15232-EP2298747A1, 15232-EP2298768A1, 15232-EP2298776A1, 15232-EP2301536A1, 15232-EP2301538A1, 15232-EP2301911A1, 15232-EP2301923A1, 15232-EP2305651A1, 15232-EP2305652A2, 15232-EP2305695A2, 15232-EP2305696A2, 15232-EP2305697A2, 15232-EP2305698A2, 15232-EP2308848A1, 15232-EP2308854A1, 15232-EP2311455A1, 15232-EP2311796A1, 15232-EP2311797A1, 15232-EP2311798A1, 15232-EP2311799A1, 15232-EP2311830A1, 15232-EP2314295A1, 15232-EP2314577A1, 15232-EP2315303A1, 15232-EP2316832A1, 15232-EP2316833A1, 15232-EP2374780A1, 15232-EP2374781A1, 15232-EP2374790A1, 15245-EP2272825A2, 15245-EP2272839A1, 15245-EP2272840A1, 15245-EP2275102A1, 15245-EP2277848A1, 15245-EP2286811A1, 15245-EP2289894A2, 15245-EP2292612A2, 15245-EP2301536A1, 15245-EP2301538A1, 15245-EP2301923A1, 15245-EP2305652A2, 15245-EP2305684A1, 15245-EP2308861A1, 15245-EP2308867A2, 15245-EP2308870A2, 15245-EP2311455A1, 15245-EP2311808A1, 15245-EP2316832A1, 15245-EP2316833A1, 18809-EP2269986A1, 18809-EP2275414A1, 18809-EP2298763A1, 18809-EP2298767A1, 18809-EP2301933A1, 18809-EP2305625A1, 18809-EP2308838A1, 18809-EP2311827A1, 18809-EP2314576A1, 18809-EP2314587A1, 19238-EP2277507A1, 19238-EP2286795A1, 19238-EP2295418A1, 19238-EP2298773A1, 19238-EP2305033A1, 19238-EP2308866A1, 19238-EP2311801A1, 19238-EP2311802A1, 19238-EP2311803A1, 19238-EP2314576A1, 19238-EP2371814A1, 91826-EP2269986A1, 91826-EP2289965A1, 91826-EP2292630A1, 91826-EP2295415A1, 91826-EP2298828A1, 91826-EP2305649A1, 91826-EP2305668A1, 91826-EP2305672A1, 91826-EP2371803A1, 91826-EP2377843A1, 100040-EP2272839A1, 100040-EP2272840A1, 100040-EP2301923A1, 102188-EP2292621A1, 102188-EP2301922A1, 157895-EP2374780A1, 157895-EP2374781A1, 4-01-00-01609 (Beilstein Handbook Reference), A838477, 3B4-0553, I14-7434, InChI=1/C4H10O/c1-4(2,3)5/h5H,1-3H, UNII-WB09NY83YA component DKGAVHZHDRPRBM-UHFFFAOYSA-N, 25-65-0

Removed Synonyms

Butyl alcohol, t Butanol, Alcohol, tert-Butyl, Alcohol, tertiary-Butyl, CID6386, c0516, (4R)-2-METHYLPENTANE-2,4-DIOL, (4S)-2-METHYL-2,4-PENTANEDIOL, D020002, TBA, 15892-23-6, MPD, MRD

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