Phthalaldehydic acid → HCID 10565146, compound

Participants

Reaction Steps

A solution of 7.50 g (50.0 mmol) 2-formylbenzoic acid, 4.89 g (40.0 mmol) DMAP and 15.42 g (100.0 mmol) geraniol in 75 ml dichloromethane was cooled in an ice bath before addition of a solution of 11.37 g (55.0 mmol) DCC in 25 ml dichloromethane, for 15 min. The reaction medium was maintained under 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×) and water (2×). The organic phase was dried over Na2SO4, concentrated and chromatographed (SiO2, 8:2 heptane/ether) to give 2.55 g (22%) (E)-3,7-dimethyl-2,6-octadienyl 2-formylbenzoate in the pure state in the form of a colourless oil.

Provenance & Evidence