Oxalyl chloride → HCID 54541172, compound

Participants

Reaction Steps

5 g (16.4 mmol) monocitronellyl (+)-phthalate was heated at reflux in 25 ml oxalyl chloride (18 eq.) for 3 h. The excess oxalyl chloride was distilled under vacuum. 5.3 g crude acid chloride was then diluted in 40 ml THF cooled to −8° under argon, and 1.87 g (3 eq.) NaBH4 was added. The reaction mixture was maintained under stirring at 0° for 4 h, then at ambient temperature for 16 h. The reaction mixture was then cooled again to 0°, and then 10 ml methanol was added dropwise. After 15 min, the mixture was poured over cold 5% KHSO4 then extracted using cold ethyl acetate. Chromatography of the crude product over silica gel (9:1 toluene/ether) yielded 1.41 g (31%) of almost pure 3,7-dimethyl-6-octenyl 2-hydroxymethylbenzoate in the form of a colourless oil.

Provenance & Evidence