3-Hydroxybenzaldehyde → HCID 18319331, compound

Participants

Reaction Conditions

Reaction Steps

3 g of bicyclo[2.2.1)hept-5-en-2-ol (27.2 mmol) and then 7.86 g of triphenylphosphine (30 mmol) are introduced at 0° C. into a solution of 3.66 g of 3-hydroxybenzaldehyde (30 mmol) in tetrahydrofuran (40 ml), and 13.6 ml of ethyl azodicarboxylate (40% in toluene, 30 mmol) are then added dropwise. The mixture is stirred at 75° C. for 48 hours, the solvent is then evaporated off, the residue is taken up in dichloromethane and the mixture is washed with normal aqueous sodium hydroxide solution, water and then saturated aqueous sodium chloride solution. The resulting solution is dried over magnesium sulfate, filtered and concentrated. The title product is isolated by chromatography on a column of silica (eluent: 88/12 cyclohexane/ethyl acetate). 0.6 g of a colorless oil is obtained:

Provenance & Evidence