Menthol → HCID 10494587, compound

Participants

Reaction Steps

A solution of 11.36 g (50.0 mmol) 2-acetylbenzoic acid, 4.88 g (40.0 mmol) DMAP and 23.40 g (150.0 mmol) (−)-menthol in 80 ml dichloromethane was cooled in an ice bath before adding a solution of 11.36 g (55.0 mmol) DCC in 40 ml dichloromethane for 15 min. The reaction mixture was maintained with stirring at 40° for 70 h. The precipitate formed during the reaction was filtered and the filtrate washed with HCl (10%, 2×) then with a saturated Na2CO3 solution (2×). The organic phase was dried (Na2SO4), concentrated, chromatographed (SiO2, toluene) and recrystallized in hexane to give 1.96 g (13%) (1R,3R,4S)-3-p-menthanyl 2-acetylbenzoate in the form of white crystals.

Provenance & Evidence