Triphenylphosphine → Hexanoic acid, 3-methyl-6-oxo-, methyl ester, (R)-

Participants

Reaction Steps

Ozone generated by a Welsbach Ozonator was passed, at -78° C., into a solution of R(+) methyl citronellate (JACS 1968, 90, 3525; 3.0 g) in MeOH (30 mL) for 1.5 h. There was added more MeOH (60 mL) and triphenylphosphine (5.13 g, 1.2 eq.) and the mixture was stirred at room temperature for 45 min. The methanol was evaporated off, the residue was diluted with Et2O (100 mL) and the insoluble phosphine oxide filtered. The filtrate material was chromatographed on silica gel, eluting with a 1:3 mixture of ethyl acetate and hexane, to afford the compound as a colorless oil (1.25 g).

Provenance & Evidence