Hydrochloric Acid → HCID 57271586, compound

Participants

Reaction Steps

A phenyllithium solution (10 ml, 27 mmol) was added dropwise over 30 min. to a rapidly stirred solution of 12-tertbutyldimethylsiloxydodecanoic acid (3.16 g, 9.6 mmol) in THF (60 ml) at 0° C. with the formation of a white precipitate. The reaction mixture was then warmed to 23° (precipitate dissolved) and stirred for 5 hours. The reaction mixture was added dropwise in three aliquots to three (0° C.) hydrolyzing solutions prepared from 20 ml 1M HCl, 4 ml CH3OH, and 16 ml H2O. The product was extracted into ethyl acetate (2×100 ml) and washed with saturated aqueous NaHCO3 followed by saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. To the crude silyl phenyl ketone (4.29 g) which was dissolved in THF (10 ml) was added tetrabutylammonium fluoride, (1M in THF, 22 ml). After this solution was stirred for 45 min. it was diluted with ethyl acetate (75 ml) and washed with 1 M HCl (100 ml), saturated aqueous NaHCO3 (100 ml) dried over Na2SO4, filtered, and concentrated in vacuo. This crude product was crystallized from ethyl acetate/hexane to yield 1.89 g of 1-phenyl-12-hydroxydodecanone in 68% yield from hydroxydodecanoic acid: mp 68° C.; 1H NMR (CDCl3) delta 7.95-7.35, (m, 5H), 3.62 (t, 2H), 2.95 (t, 2H), 1.28 (br s, 18H).

Provenance & Evidence