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

Participants

Reaction Steps

A solution of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol (0.2 g, 0.72 mmol, from Example 5.1, Step 6) in 1.5 mL of CCL4 and 2.2 mL of water containing 4 mg RuCl3 was treated with 628 mg, 2.94 mmol of NaIO4. The mixture was stirred at room temperature for 2.5 h, diluted with 10 mL of water and the pH adjusted to 2 with 10% aqueous HCl. The mixture was extracted with dichloromethane, concentrated to dryness, and purified via flash chromatography (0-20% ethyl acetate/hexane gradient elution) to give 105 mg (50%) of 2-(4,4-dimethyl-chroman-7-yl)-heptanoic acid.

Provenance & Evidence