Sodium hydride → HCID 22858136, compound

Participants

Reaction Steps

Thereafter, 0.09 g of 60% sodium hydride was suspended in 5 ml of dimethylformamide, and a solution of 0.63 g of 4'-octyloxybiphenol in 5 ml of dimethylformamide was added to the suspension, and the mixture was stirred at room temperature for 1 hr to conduct a reaction. To the resultant solution was added 0.60 g of 2-iodomethyl-5,5-dimethyl-δ-valerolactone, and stirring was continued at room temperature for two days to conduct a reaction. The reaction mixture was poured into ice water, and the reaction product was extracted with diethyl ether. The extract was washed three times with water and dried over magnesium sulfate, the solvent was removed by distillation under a reduced pressure to obtain a crude product, and the crude product was purified by a silica gel column chromatography to 0.58 g of 2-(4'-octyloxybiphenyloxymethyl)-5,5-dimethyl-δ-valerolactone. The product was subjected to optical resolution by a liquid chromatography, and both components thus obtained were each recrystallized from ethanol to obtain 0.20 g of (2R)-2-(4 '-octyloxybiphenyloxymethyl)-5,5-dimethyl-δ-valerolactone and 0.11 g of (2S)-2-(4'-octyloxybiphenyloxymethyl)-5,5-dimethyl-δ-valerolactone, respectively.

Provenance & Evidence