3-Hydroxybenzaldehyde → 3-formylphenyl 2-acetoxybenzoate

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Reaction Steps

A mixture of 3-hydroxybenzaldehyde (830 g) and triethylamine (8.24 g) in methylene chloride (12.6 l) is kept under stirring, in inert nitrogen atmosphere, cooling at a temperature between −5° C. and 0° C. Salicyloyl chloride (1650 g) is added in small portions in an hour. The mixture is still kept under stirring for 15 minutes, then water (10 l) is added and the phases are separated. The aqueous phase is recovered and apart extracted with methylene chloride (3 l). The organic phases are joined together, washed with a 5% Na2CO3 solution (5 l×2 times) and then with water (5 l×2 times). The organic phase is dried with magnesium sulphate (2 Kg) in the presence of decolorating carbon (300 g). It is filtered under vacuum and the solvent is evaporated at reduced pressure at a bath temperature lower than 40° C., at last obtaining 1929 g of 3-(formyl)phenyl ester of the 2-(acetoxy) benzoic acid (quantitative yield) m.p. 80-84° C. The compound purity determined by HPLC, by using a LiChrospher® 100 RP 8 column, eluent buffer phosphate pH 8/acetonitrile 55/45, was equal to 98.5%.

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