Hydrochloric Acid → HCID 18177877, compound

Participants

Reaction Conditions

Reaction Steps

The ester (609 mg) was dissolved in 9 ml of ethanol and treated with 1.59 g of potassium hydroxide in 6 ml of water. The heterogeneous mixture was further treated with 4 ml of THF and the resulting clear solution was heated to 45° C. for 1.5 hour. The mixture was diluted with 20 ml of water and the pH was adjusted to 2 with HCl 25%. The mixture was extracted with 3 portions of 25 ml of ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The resulting orange oil was purified by flash chromatography (SiO2, 25% ethyl/hexanes) followed by trituration in pentane, giving 290 mg of (RS)-4-[3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-oct-1-ynyl]-benzoic acid as a white solid, m.p. 115-116° C.

Provenance & Evidence