Sodium Hydroxide → Tert-butyl (cis-3-methoxymethoxycyclohexylmethoxy)acetate

Participants

Reaction Conditions

Reaction Steps

1.0 g of (cis-3-methoxymethoxycyclohexyl)methanol and 3.3 g of tert-butylbromoacetate are dissolved in 30 ml of toluene, and 0.50 g of tetrabutylammonium hydrogensulfate is added. The suspension is cooled to 10° C. 10 ml of 50% strength NaOH are added to the suspension. The mixture is allowed to warm to room temperature, and after 3 h the aqueous phase is 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 1.10 g of tert-butyl (cis-3-methoxymethoxycyclohexylmethoxy)acetate as a colorless oil. C15H28O5 (288), LCMS(ESI): 306 (M++H2O).

Provenance & Evidence