Citronellol → HCID 10733156, compound

Participants

Reaction Steps

A solution of 6.49 g (30.0 mmol) 2-acetylbenzoic acid, 3.81 g (31.2 mmol) DMAP and 12.48 g (80.0 mmol) citronellol in 60 ml dichloromethane was cooled in an ice bath before adding a solution of 8.84 g (42.9 mmol) DCC in 40 ml dichloromethane over 5 min. The reaction mixture was maintained with stirring at 40° for 75 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 (Na2SO4), and the solvent evaporated. The excess citronellol was distilled (1 Torr, 60-80°), and the residue chromatographed (SiO2, 9:1 toluene/ethyl acetate) and distilled (0.6 Torr, 150-155°), to give 7.43 g (63%) of 3,7-dimethyl-6-octenyl 2-acetylbenzoate in the form of a colourless oil.

Provenance & Evidence