Benzyl Bromide → HCID 10614463, compound

HRID 1081313Notes

Reaction equation

HRID 1081313 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C[O-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O>CC(C)=O.CO>[CH2:20]([O:1][C:2]1[CH:16]=[CH:15][C:5]([C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 691504,4'-DihydroxybenzophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 10614463HCID 10614463, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

To a solution of 2.0 g (9.3 mmol) of 4,4'-dihydroxybenzophenon in 50 ml dry acetone was added 27.5 ml of 0.34M NaOMe in MeOH. After the reaction mixture had been stirred for 20 min, 1.6 g (9.3 mmol) of benzylbromide was added. The reaction was stirred at room temperature for 15 h. 250 ml EtOAc was added and then extracted with 2×50 ml 0.5M HCl, 2×50 ml H2O and 50 ml saturated NaCl(aq). Drying (MgSO4), evaporation of the EtOAc and purification on silica gave 0.93 g (33%) of 4'-benzyloxy-4-hydroxy benzophenon.

Workup

  1. stirringThe reaction was stirred at room temperature for 15 h
  2. extractionextracted with 2×50 ml 0.5M HCl, 2×50 ml H2O and 50 ml saturated NaCl(aq)
  3. customDrying
  4. custom(MgSO4), evaporation of the EtOAc and purification on silica

Sources & evidence

ORD record
ord-aa164798f25d4acfbce38309fbc5299d
Source dataset
uspto-grants-1996_12
Patent number
US05585404

Reaction notes

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