Synthesis of benzal diacetate

Preparation of benzal diacetate

Ten grams (0.094 mole) of benzaldehyde (free of benzoic acid) is added to a mixture of 10.6 g. (10% excess) of acetic anhydride and 0.1 g. of concentrated sulfuric acid. The mixture is agitated and cooled so the temperature does not rise above 70°. The mixture is allowed to stand 24 hours at room temperature. It is then dissolved in ether, and the resulting solution is extracted with water, dilute sodium carbonate solution, and again with water. After being dried over sodium sulfate the ethereal solution is distilled. There is obtained 16 g. (81%) of the diacetate, b.p. 154°/20 mm., m.p. 46°.

Reference: Knoevenagel, Ann., 402, 117 (1913).

IUPAC Name

[acetyloxy(phenyl)methyl] acetate

InChI

InChI=1S/C11H12O4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7,11H,1-2H3

InChI Key

XRYSDRCNTMEYFH-UHFFFAOYSA-N

Canonical SMILES

CC(=O)OC(C1=CC=CC=C1)OC(=O)C

Depositor-Supplied Synonyms

Benzal diacetate, 581-55-5, Benzylidene diacetate, Phenylmethylene diacetate, Methanediol, phenyl-, diacetate, XRYSDRCNTMEYFH-UHFFFAOYSA-N, ST50825562, EINECS 209-469-8, AI3-19329, Diacetic acid benzylidene, phenylmethanediyl diacetate, Phenylmethanediol diacetate, ACMC-1AMT8, alpha,alpha-Diacetoxytoluene, acetyloxyphenylmethyl acetate, SCHEMBL486678, AC1L29U7, (acetyloxy-phenylmethyl) acetate, CTK8B1957, [acetyloxy(phenyl)methyl] acetate, DTXSID60206824, NSC7732, MolPort-001-783-240, NSC-7732, ZINC1688330, (Acetyloxy)(phenyl)methyl acetate #, ANW-32891, MFCD00059206, STL386374, ZINC01688330, AKOS022176672, MCULE-5843191462, VZ31264, AJ-29930, AK142809, CC-24284, OR051528, OR288932, AX8013146, TC-121636, B0010, C-10587, InChI=1/C11H12O4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7,11H,1-2H

Removed Synonyms

Benzaldiacetate, CID68489, C11-H12-O4

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