Hydrochloric Acid → 9-Phenylheptadecan-9-ol

Temperature

0 °C

Methyl benzoate (14.34 g, 105.3 mmol) was dissolved in anhydrous THF (43 mL) and this mixture was cooled to 0° C. A solution of n-octylmagnesiumchloride in THF (200.0 mL, 2.0M, 400 mmol) was then added dropwise, keeping the temperature at less than 10° C. Upon completion of addition, the mixture was left to stir at 0° C. for 2 hours. A solution of hydrochloric acid in water (400 mL, 1.0 M) was then added dropwise keeping the temperature at less than 25° C. The mixture was diluted with iProAc (420 mL) and the resulting organic layer was washed with 1.0 M HCl (1×70 mL), washed with brine (1×70 mL), dried over sodium sulfate and evaporated to yield a colorless liquid. The crude material was purified by silica gel column chromatography to afford a clear colorless liquid (21.0 g). 1H NMR (300 MHz, CDCl3, δ): 7.41-7.30 (m, 4H), 7.28-7.20 (m, 1H), 1.90-1.70 (m, 4H), 1.35-1.20 (m, 23H), 1.11-0.96 (m, 2H) and 0.92-0.83 (m, 6H).

1. customat less than 10° C
2. additionUpon completion of addition
3. waitthe mixture was left
4. customat less than 25° C
5. additionThe mixture was diluted with iProAc (420 mL)
6. washthe resulting organic layer was washed with 1.0 M HCl (1×70 mL)
7. washwashed with brine (1×70 mL)
8. dry with materialdried over sodium sulfate
9. customevaporated
10. customto yield a colorless liquid
11. customThe crude material was purified by silica gel column chromatography

ORD record

ord-95b277749d0846a091e1495c9547489a

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933225B2