Ammonium Chloride → Dimethyl 4,4'-[2-(hydroxymethyl)butane-1,4-diyl]dibenzoate

Participants

Reaction Conditions

Reaction Steps

112.8 ml (112.8 mmol) of a 1 M boran-THF complex solution are added dropwise to a solution of 20.9 g (56.4 mmol) of 2-[4-(methoxycarbonyl)benzyl]-4-[4-(methoxycarbonyl)phenyl]butanoic acid in 600 ml of THF at −10° C. The reaction mixture is then warmed to 0° C. and stirred at this temperature for 4 h. After reaction is complete, saturated ammonium chloride solution is added to the reaction mixture, which is diluted with water and ethyl acetate, the phases are separated, and the aqueous phase is back-extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulphate and, after filtration, freed of solvent in vacuo. 20.11 g (94% purity, 100% of theory) of a colourless solid are obtained.

Provenance & Evidence