(1R)-3-chloro-1-phenylpropan-1-ol → (R)-3-phthalimido-1-phenylpropanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 10.09 g of (R)-(+)-3-chloro-1-phenylpropanol in 80 ml of dimethylformamide were added 13.14 g of potassium phthalimide in 80 ml of dimethylformamide. The mixture was heated at 100° C. for 8 hours, allowed to cool to room temperature, and filtered. The filtrate was diluted with water, and the solution extracted 3 times with ethyl acetate. The combined organic extracts were washed once with water, once with 0.2 N sodium hydroxide, once again with water, and once with a saturated solution of sodium chloride, dried over sodium sulfate, and concentrated in vacuo to provide an opaque oil that solidified. Crystallization from ethyl acetate/hexanes provided 11.09 g of the title intermediate as clear pale yellow needles, m.p. 81°-83° C.

Provenance & Evidence