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

Temperature

0 °C

4-Butyrolactone (11.93 mL, 0.155 mol) was dissolved in anhydrous THF and cooled to 0° C. Phenylmagnesium bromide (3 M in ether, 112 mL) was added dropwise over 30 minutes to the reaction under N2. After the addition, the reaction was warmed to room temperature overnight. Additional phenylmagnesium bromide (3 M in ether, 103 mL) was added, and the reaction stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl (150 mL). Ether (200 mL) and 10% HCl (100 mL) were added. The organic layer was separated and washed with 10% HCl (100 mL), brine (100 mL), and then dried over MgSO4. The solution was filtered, concentrated, and the crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes to give 26.94 g (72%) of desired product as an off-white solid.

1. additionAfter the addition
2. temperaturethe reaction was warmed to room temperature overnight
3. customThe reaction was quenched with saturated NH4Cl (150 mL)
4. additionEther (200 mL) and 10% HCl (100 mL) were added
5. customThe organic layer was separated
6. washwashed with 10% HCl (100 mL), brine (100 mL)
7. dry with materialdried over MgSO4
8. filtrationThe solution was filtered
9. concentrationconcentrated
10. customthe crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes

ORD record

ord-3e535bf6cec64844967c9300f4871469

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05932573