Benzyl Alcohol → 9-(Benzyloxy)-9-oxononanoic acid

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Reaction Steps

Toluene-4-sulfonic acid monohydrate (0.71 g, 3.72 mmol) is added to a suspension of azelaic acid (25.0 g, 132.82 mmol) in benzene (550 ml). The mixture is heated to 80° C., whereafter benzyl alcohol (14.36 g, 132.82 mmol) in benzene (50 ml) is added dropwise to the resulting solution. The reaction mixture is refluxed overnight and water is removed azeotropically with a Dean Stark trap. The reaction mixture is allowed to cool, the white precipitate which forms is removed by filtration and the filtrate is concentrated to a brownish oil under reduced pressure. The crude product (33.97 g) is dissolved in dichloromethane (50 ml) and purified by flash chromatography, on a 5.5×15 cm silica column with dichloromethane/methanol (20:1) as eluant. The product, a yellow oil, is dried under vacuum. The oil crystallizes after a few hours at room temperature. Yield: 12.8 g (35%). 13C NMR (75 MHz, CDCl3): δ 24.5, 24.8, 28.8, 34.0, 34.2, 66.1, 128.2, 128.5, 136.1, 173.6, 180.0.

Provenance & Evidence