Dihydrocoumarin → Chroman-2-ol

Participants

Reaction Conditions

Reaction Steps

Dihydrocoumarin (5 g, 33.74 mmol) was dissolved in 50 mL of toluene and cooled to −78° C. Dibal (1 M solution in toluene, 38 mL, 38 mmol) was added to the reaction flask over a 45 minutes period. The reaction mixture was stirred at this temperature for 2 h. Water (50 mL) was added slowly along with some toluene to ensure a smooth stirring of the reaction mixture. The slurry was warmed to room temperature and stirring was continued overnight. The organic layer was decanted and dried with magnesium sulfate. Solvent was removed via rotatory evaporator to give compound 5A as a clear oil (4.5 g, 89%). MS: 149 (M−1)+

Provenance & Evidence