Hydrochloric Acid → 2-(4,4-Dimethyl-chroman-7-yl)-heptanoic acid

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Reaction Steps

To a solution of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol (0.27 g, 0.98 mmole, from Example 1, step 6) in a mixture of 2 mL of carbon tetrachloride, 2 mL acetonitrile and 3 mL water, containing 3-5 mg of ruthenium chloride, was added 0.85 g of sodium periodate. The mixture was stirred at room temperature for 2 hours, diluted with 10 mL of water, and pH was adjusted to 2 with 10% hydrochloric acid. The mixture was extracted with three 10 mL portions of dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a dark oil. The product was purified by flash chromatography (SiO2, gradient from 0 to 20% ethyl acetate in hexanes) to yield 0.16 g of 2-(4,4-dimethyl-chroman-7-yl)-heptanoic acid as a pale yellow oil.

Provenance & Evidence