Dimethyl Sulfoxide → HCID 86746502, compound

Participants

Reaction Conditions

Reaction Steps

A dichloromethane solution (25 ml) of oxalyl chloride (1 ml, 11 mmole) was cooled to -70° C. under an atmosphere of argon, and a solvent mixture of DMSO (1.7 ml, 22 mmole) and dichloromethane (5 ml) was added dropwise to the solution, while maintaining its temperature at not higher than -60° C. Subsequently, a dichloromethane solution (10 ml) of 3-(3,5,6-trimethyl-1,4-dimethoxybenzyl)-butan -1-ol (3 g, 11 mmole) was added dropwise to the mixed solution, followed by stirring at -70° C. for 15 minutes, and triethylamine (7 ml, 50 mmole) was added dropwise. Then, stirring was continued until the temperature of the reaction solution reached the room temperature, and water (50 ml) was added to the reaction solution, followed by concentration under reduced pressure. The residue was extracted with IPE, and the organic layer was washed with IPE, dried and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give 3-(3,5,6-trimethyl-1,4-dimethoxybenzyl)butanal (2.7 g, 90%). δ9.68(1H,t), 3.83(1H,m), 2.67(3H,s), 3.60(3H,s), 2.89 (2H,dd,2Hz,6Hz), 2.27(3H,s), 2.16(6H,s), 1.33(3H,s).

Provenance & Evidence