Benzophenone → alpha,alpha-Diphenylbenzeneethanol

HRID 1818678Notes

Reaction equation

HRID 1818678 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOCC>[C:11]1([C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:17])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 7498Benzyl BromideHCID 5462224Magnesium

Product 1

HCID 245013alpha,alpha-DiphenylbenzeneethanolYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of Mg (1.7 g, 0.07 mol) in dry ether (25 mL) was added a solution of benzyl bromide (10 mL, 1.5 equ.) in dry ether (25 mL) drop-wise and allowed to stir at RT for 1 h. By the time all magnesium was dissolved and the reaction mixture was cooled to 0° C. To this was added a solution of benzophenone (10 g, 0.05 mol) in dry ether (25 mL) and allowed to stir at RT for 5 h. The progress of the reaction was followed by TLC and when it was ready the reaction mixture was quenched with saturated NH4Cl solution, extracted with ether (100 mL), washed with brine, dried and concentrated under vacuum. The crude product was purified by column chromatography on silica gel (10% ethyl acetate in pet. ether) to give the title compound (9.6 g, 65%) as a white solid.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringto stir at RT for 5 h
  3. customwas quenched with saturated NH4Cl solution
  4. extractionextracted with ether (100 mL)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by column chromatography on silica gel (10% ethyl acetate in pet. ether)

Sources & evidence

ORD record
ord-9310c1c629d2486791e3c880ee4703e7
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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