Gamma-Butyrolactone → 1,1-Diphenylbutane-1,4-diol

Temperature

-78 °C

A solution of butyrolactone (10.5 g, 122 mmol) in anhydrous THF (500 mL) was chilled to −78° C. under nitrogen atmosphere. Phenylmagnesium bromide (3M in ether, 100 mL, 300 mmol) was added via syringe at a rate that keeps the reaction temperature below −40° C. After the addition was complete, the reaction was stirred at −78° C. for two hours then the cold bath was removed and the reaction mixture was allowed to warm to room temperature overnight. The solution was then re-cooled to 10° C. on an ice bath before adding 2N aqueous ammonium chloride (200 mL) to quench the reaction. The resulting mixture was diluted with ethyl acetate (1 L) and the organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered. Evaporation of solvent from the filtrate afforded crude 1,1-diphenylbutan-1,4-diol as an oil, which was purified by chromatography on silica gel, eluting with a gradient of 50% to 60% ethyl acetate in hexane. Evaporation of solvents gave a colorless solid that was triturated with hexane and collected by filtration to afford 18.2 g of pure 1,1-diphenylbutan-1,4-diol. MS (EI+): 243 (M+1); 225 (M-H2O+1).

1. customthe reaction temperature below −40° C
2. additionAfter the addition
3. customthe cold bath was removed
4. temperatureto warm to room temperature overnight
5. temperatureThe solution was then re-cooled to 10° C. on an ice bath
6. additionbefore adding 2N aqueous ammonium chloride (200 mL)
7. customto quench
8. customthe reaction
9. customthe organic layer was separated
10. washwashed with saturated aqueous sodium chloride
11. dry with materialdried over anhydrous sodium sulfate
12. filtrationfiltered
13. customEvaporation of solvent from the filtrate
14. customafforded crude 1,1-diphenylbutan-1,4-diol as an oil, which
15. customwas purified by chromatography on silica gel
16. washeluting with a gradient of 50% to 60% ethyl acetate in hexane
17. customEvaporation of solvents
18. customgave a colorless solid
19. customthat was triturated with hexane
20. filtrationcollected by filtration

ORD record

ord-230498b824c74e548b05978ef5dd865c

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960526B2