From: Raman Parkesh (parkesh101$##$yahoo.com)
Date: Sun Mar 12 2006 - 12:26:41 EST
Hi Nalini
This is one of the method from JOC 1978, 2093, where Acetic anhydride and pyridine is used. However you can very easily substitue with acetyl chloride and triethyamine or pyridine and it would work fine.
Regards
Raman
m-Acetoxybenzaldehyde
In a 250-mL flask, equipped with a
magnetic stirring bar and calcium sulfate drying tube, was charged
with 25.0 g (0.205 mol) of m-hydroxybenzaldehyde and 100 mL of
pyridine followed by 25.0 mL of acetic anhydride. After stirring at
room temperature for 40 min, the reaction mixture was diluted with
brine and ice and extracted with ethyl acetate (2x1. The combined
extracts were washed with 1.2 N aqueous hydrochloric acid (ex),
saturated aqueous sodium bicarbonate (2x1, and brine, and dried over
magnesium sulfate. Concentration in vacuo gave 32.52 g of a redorange
oil which was distilled at reduced pressure to give 24.95 g (74%)
of pure 16: bp 100 "C (1.0 mm). The NMR spectrum showed absorptions
at 6 2.25 (s, 3 H), 7.1-7.8 (m, 4 H), 9.78 (s, 1 H).
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