Methanone, 1,3-phenylenebis[phenyl- → HCID 85856804, compound

HRID 333198Notes

Reaction equation

[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[C:1]([C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH:15]([OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1,3 dibenzoylbenzene 2 (2.00 g, 6.98 mmol) was dissolved in anhydrous ethanol (20 mL) under an inert atmosphere of nitrogen gas. The reaction mixture was cooled to 0° C. followed by the addition of sodium borohydride (0.090 g, 2.094 mmol). The reaction mixture was stirred for 4 h and quenched the addition of a small amount of water. The reaction mixture was concentrated under reduced pressure and the products were extracted from water with ethyl acetate (2×50 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 93:7 to 30:70) afforded 3-benzoyl benzhydrol 5 (0.601 g, 2.084 mmol) in a 30% yield.

Workup

customquenched
additionthe addition of a small amount of water
concentrationThe reaction mixture was concentrated under reduced pressure
extractionthe products were extracted from water with ethyl acetate (2×50 mL)
washThe combined organic phases were washed with brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was removed under reduced pressure
customPurification

Sources & evidence

ORD record: ord-61a944f91f9940deb26073d7f1eed2ec
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877967B2

Reaction notes

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