4-Hydroxybenzaldehyde → Benzaldehyde, 4-(phenylmethoxy)-

HRID 2422260Notes

Reaction equation

HRID 2422260 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)(=O)C.CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-hydroxybenzaldehyde (28.2 g, 231 mmol), potassium carbonate (47.9 g, 347 mmol), potassium iodide (3.84 g, 23.1 mmol) and N,N-dimethylformamide (280 mL) was added benzyl bromide (27.5 mL, 231 mmol) with stirring at room temperature, and the mixture was stirred at the same temperature for 24 hrs. The reaction mixture was diluted with ethyl acetate, washed successively with water, 1N hydrochloric acid and saturated brine, dried, and concentrated under reduced pressure to give the title compound (48 g, yield 98%) as beige crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 24 hrs
  2. washwashed successively with water, 1N hydrochloric acid and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-910835eaaaf14f78829746235d319619
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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