Hydrochloric Acid → HCID 57271586, compound

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).

1. temperatureThe reaction mixture was then warmed to 23°
2. dissolution(precipitate dissolved)
3. additionThe reaction mixture was added dropwise in three aliquots to three (0° C.) hydrolyzing solutions
4. extractionThe product was extracted into ethyl acetate (2×100 ml)
5. washwashed with saturated aqueous NaHCO3
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. dissolutionTo the crude silyl phenyl ketone (4.29 g) which was dissolved in THF (10 ml)
10. additionwas added tetrabutylammonium fluoride, (1M in THF, 22 ml)
11. stirringAfter this solution was stirred for 45 min. it
12. additionwas diluted with ethyl acetate (75 ml)
13. washwashed with 1 M HCl (100 ml), saturated aqueous NaHCO3 (100 ml)
14. dry with materialdried over Na2SO4
15. filtrationfiltered
16. concentrationconcentrated in vacuo
17. customThis crude product was crystallized from ethyl acetate/hexane

ORD record

ord-00e4b3e0916f4972960cb0e0c62d2115

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06022714