Sodium Hydroxide → Benzoic Acid

Participants

Reaction Steps

To a biphasic mixture of 25.0 gm of the compound of Example 2 (69 mmol, 1.0 equiv.) in 125 mL of toluene was added 2.75 gm of sodium hydroxide (69 mmol, 1.0 equiv.) dissolved in 20 mL of water followed by 8.27 gm (69 mmol, 1.0 equiv.) of (S)-styrene oxide. The reaction mixture was heated to reflux overnight, at which time HPLC analysis showed that only trace starting material remained. Upon cooling to room temperature the layers were separated. The organic layer was washed with an additional 1.4 gm (35 mmol, 0.5 equiv.) of sodium hydroxide dissolved in 20 mL of water followed by another wash with 20 mL of water. The toluene solvent was removed under vacuum to provide 19.77 gm (92%) of a thick oil which solidified on standing. The crude product contained an ~1.2:1.0 mixture of regioisomers and was used without further purification in the next step.

Provenance & Evidence