Benzyl Bromide → HCID 10614463, compound

HRID 865678Notes

Reaction equation

HRID 865678 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 2150 ml 0.5M HCl, 2150 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 2150 ml 0.5M HCl, 2150 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-5d31294505ff4779a14b7bb64d914fbb
Source dataset
uspto-grants-1996_10
Patent number
US05567728

Reaction notes

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