Formic Acid → Methyl 4-(2-carboxy-6-cyanohexyl)benzoate

Participants

Reaction Conditions

Reaction Steps

17.24 ml (123.71 mmol) of triethylamine and 4.24 ml (112.46 mmol) of formic acid in 500 ml of dioxane is added to a solution of 15.5 g (37.49 mmol) of diallyl 2-(4-cyanobutyl)-2-(4 methoxycarbonylbenzyl)malonate from Example 115A, 690 mg (2.62 mmol) of triphenylphosphine and 170 mg (0.75 mmol) of palladium acetate in 500 ml of dioxane at room temperature. The reaction mixture is then stirred at 10° C. for 12 hours. After conversion is complete, the reaction solution is cooled and the solvent is removed in vacuo. The residue is then taken up in ethyl acetate and water and acidified with 1 N hydrochloric acid and the organic phase is separated off. The aqueous phase is extracted three times more with ethyl acetate, and then the organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solution is concentrated in vacuo. 8.1 g (74% yield) of a colorless solid are obtained.

Provenance & Evidence