Benzyl Alcohol → 1-(Benzyloxycarbonyl)cyclopropanecarboxylic acid

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Reaction Steps

1,1-Cyclopropanedicarboxylic acid (5.02 g) was dissolved in tetrahydrofuran (50 ml) under a nitrogen atmosphere, and triethylamine (5.38 ml) was added dropwise with stirring and cooling in an ice water bath. After stirring at the same temperature for 30 minutes, thionyl chloride (2.82 ml) was added dropwise with cooling in ice water bath. After stirring at the same temperature for 30 minutes, a solution of benzyl alcohol (4.39 ml) in tetrahydrofuran (25 ml) was added with cooling in an ice water bath, and the reaction mixture was gradually brought to room temperature and stirred overnight. A 2N aqueous solution of sodium hydroxide (100 ml) was added to the reaction mixture, and tetrahydrofuran was distilled off under reduced pressure. tert-Butyl methyl ether (25 ml) was added to the resultant aqueous solution, followed by stirring. The organic layer and the aqueous layer were separated. The aqueous layer was cooled in an ice water bath, and 2N hydrochloric acid (50 ml) was added to adjust pH 4. Ethyl acetate (150 ml) was added, and the reaction mixture was stirred for a while. The organic layer was separated, washed with brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent was dried under reduced pressure to give the title compound (6.29 g, 74%) as a pale yellow oil.

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