Dimethyl Sulfide → (Z)-6-((4-methoxybenzyl)oxy)-4-methylhex-4-enal

Participants

Reaction Steps

1-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzene (75.0 g, 273 mmol) was dissolved in dichloromethane (1.13 l) and pyridine (11.3 ml). This reaction solution was cooled to −78° C., to which ozone was bubbled (flow rate 2 l/min, electric voltage 90 V) for 170 minutes with stirring. After addition of dimethylsulfide (80.3 ml, 1.09 mol), the reaction solution was allowed to warm to room temperature and was stirred overnight. The reaction solution was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1) and the title compound (36.9 g) was obtained as a colorless oil while 1-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzene (14.1 g) was recovered.

Provenance & Evidence