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ChemicalBook CAS DataBase List Cinnamyl acetate
103-54-8

Cinnamyl acetate synthesis

13synthesis methods
By direct esterification of cinnamic alcohol with acetic acid (or anhydride) under azeotropic conditions (Arctander, 1969).
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Yield:103-54-8 97%

Reaction Conditions:

with toluene-4-sulfonic acid in acetonitrile at 20; for 16 h;

Steps:

General procedure for the protection of alcohols 1 as acetyl-derivatives.
General procedure: A mixture of the alcohol 1 (1 mmol), isopropenyl acetate (0.45 mL, 4 mmol) and p-TsOH (4 mg, 0.02 mmol) in dichloromethane or acetonitrile (4 mL) was stirred the indicated temperature (see Tables 1 and 2). Reaction times ranged from 16 to 36 h. After completion of the reaction (TLC monitoring) the mixture was poured into 10 mL of 10% aqueous sodium hydrogen carbonate solution. The aqueous phase was extracted with ethyl acetate (3 × 10 mL) and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate and then evaporated under vacuum. Purification by silica gel column chromatography afforded the pure acetyl ester 2. Physical and spectral data of known compounds were consistent with the ones reported in literature. Physical and spectral data of not previously described compounds are reported below.

References:

Temperini, Andrea;Minuti, Lucio;Morini, Tommaso;Rosati, Ornelio;Piazzolla, Francesca [Tetrahedron Letters,2017,vol. 58,# 43,p. 4051 - 4053]

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