Water → 4-Benzyloxybenzophenone

HRID 70735

Reaction equation

HRID 70735 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:6][CH:5]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:8][CH:9]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 143474-HydroxybenzophenoneHCID 24758Sodium hydride

Product 1

HCID 4581934-Benzyloxybenzophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in mineral oil, 1.2 g, 30 mmol) was added to an ice-cooled solution of (4-hydroxy-phenyl)-phenyl-methanone (5 g, 25.2 mmol) in DMF (25 mL). Stirred for 20 minutes at room temperature. Benzyl bromide (6.1 ml, 50 mmol) was added at 0° C. The reaction temperature was raised to room temperature after 1 h. Stirred 2 h. Water (20 mL) was added and aqueous phase was extracted dichloromethane (2×30 mL). The combined organic phase was concentrated and purified by flash chromatography (eluent: dichloromethane). 1H nmr revealed the product was pure. Yield: 7.0 g, 96%

Workup

  1. temperatureThe reaction temperature was raised to room temperature after 1 h
  2. stirringStirred 2 h
  3. extractionaqueous phase was extracted dichloromethane (2×30 mL)
  4. concentrationThe combined organic phase was concentrated
  5. custompurified by flash chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-18532b48adef474fa62a79baa547041c
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Linked notes

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