Sodium Hydroxide → Tert-butyl [cis-3-(methoxymethoxymethyl)cyclohexylmethoxy]acetate

Participants

Reaction Conditions

Reaction Steps

1.65 g of (cis-3-methoxymethoxymethylcyclohexyl)methanol and 5.1 g of tert-butyl bromoacetate are dissolved in 20 ml of toluene, and 1.50 g of tetrabutylammonium hydrogensulfate are added. The suspension is cooled to 10° C. 20 ml of 50% NaOH are added to the suspension. The mixture is stirred at 10° C. for 6 h and the aqueous phase is then removed and extracted with methyl tert-butyl ether. The combined organic phases are dried over MgSO4 and concentrated. Flash column chromatography on silica gel (heptane/ethyl acetate 10/1→2/1) gives 2.23 g of tert-butyl [cis-3-(methoxymethoxymethyl)cyclohexylmethoxy]acetate as a colorless oil.

Provenance & Evidence