Phthalaldehydic acid → Benzoic acid, 2-formyl-, 3,7-dimethyl-6-octenyl ester

Participants

Reaction Steps

A solution of 7.50 g (50.0 mmol) 2-formylbenzoic acid, 4.88 g (40.0 mmol) 4-dimethyl aminopyridine (DMAP) and 15.60 g (100.0 mmol) citronellol in 75 ml dichloromethane was cooled in an ice bath before addition of a solution of 11.35 g (55.0 mmol) dicyclohexylcarbodiimide (DCC) in 25 ml dichloromethane for 15 min. The reaction medium was maintained with stirring at 0° for 15 min, then at 20° for 48 h. The precipitate formed during the reaction was filtered and the filtrate washed with HCl (10%, 2×) and with a saturated Na2CO3 solution (2×). The organic phase was dried over Na2SO4, concentrated and chromatographed twice (SiO2, ethyl toluene/ethyl acetate 19:1 and SiO2, toluene) to give 2.25 g (16%) 3,7 dimethyl-6-octenyl 2-formylbenzoate in the pure state in the form of a colourless oil.

Provenance & Evidence