Synthesis of tert-butyl acetate

Preparation of tert-butyl acetate

tert-Butyl acetate is prepared by reacting tert-butyl alcohol with acetic anhydride

Preparation of tert-butyl acetate

Preparation of tert-butyl acetate

To the round bottom flask fitted with a reflux condenser, thermometer, and mechanical stirrer a mixture of 61.2 g of acetic anhydride and 27 g of finely pulverized calcium carbide are placed. The mixture is refluxed for 2 hours and after cooling to 70° C, 29.6 g of dry tert-butyl alcohol is added and the mixture is refluxed for 4 day. After reaction is complete the mixture is cooled and the thick slurry is decomposed by careful addition to ice. tert-Butyl acetate is purified by steam distillation, ester layer washed with diluted solution of sodium carbonate, water and dried over anhydrous magnesium sulfate. Pure tert-butyl acetate is obtained by fractional distillation yielding 80-90% of product with boiling point 95-96.5° C.

Advanced Organic Synthesis, R. S. Monson, 62, 1971

IUPAC Name

tert-butyl acetate

InChI

InChI=1S/C6H12O2/c1-5(7)8-6(2,3)4/h1-4H3

InChI Key

WMOVHXAZOJBABW-UHFFFAOYSA-N

Canonical SMILES

CC(=O)OC(C)(C)C

MeSH Synonyms

tert-butyl acetate

Depositor-Supplied Synonyms

TERT-BUTYL ACETATE, 540-88-5, t-Butyl acetate, tert-Butyl ethanoate, Texaco lead appreciator, Acetic acid, tert-butyl ester, Acetic acid, 1,1-dimethylethyl ester, 1,1-dimethylethyl acetate, Acetic Acid tert-Butyl Ester, tert.-Butyl acetate, 1,1-Dimethyl acetate, NSC 59719, UNII-76N22HKP3X, CCRIS 8999, HSDB 835, WMOVHXAZOJBABW-UHFFFAOYSA-N, EINECS 208-760-7, BRN 1699506, tert-butylacetat, tertbutyl acetate, tert butyl acetate, tertiary butyl acetate, tertiary-butyl acetate, ACMC-1AVPI, Acetic acid t-butyl ester, DSSTox_CID_2055, AC1L1W7H, AC1Q5XJ3, DSSTox_RID_76472, DSSTox_GSID_22055, SCHEMBL26684, B88209_ALDRICH, KSC492I1F, acetic acid tert.-butyl ester, CH3C(O)OC(CH3)3, 76N22HKP3X, CHEMBL3186747, CTK3J2412, WLN: 1X1&1&OV1, Acetic acid,1-dimethylethyl ester, MolPort-001-759-863, LTBB002238, ACN-S002402, NSC59719, Tox21_301308, ANW-31950, NSC-59719, ZINC00388665, AKOS009031236, RP19233, RTR-019125, NCGC00255313-01, AN-21332, BC207665, CAS-540-88-5, CJ-03319, LS-11209, SC-22684, ZB011643, acetic acid tert-butyl estert-butyl acetate, KB-204631, TL8003551, TR-019125, FT-0621760, C-6050, 4-02-00-00151 (Beilstein Handbook Reference), A829954, tert-Butyl acetate [UN1123] [Flammable liquid], tert-Butyl acetate [UN1123] [Flammable liquid], 3B4-0100, I04-0250, InChI=1/C6H12O2/c1-5(7)8-6(2,3)4/h1-4H

Removed Synonyms

tert-butylacetate, t-BUTYLACETATE, tert-Butoxy acetic acid, UN 1123 (Related), UN1123, CID10908, A0026, TLA, 13211-32-0

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