Benzyl Bromide → 2-Benzyloxy-5-phenoxybenzaldehyde

HRID 892845Notes

Reaction equation

HRID 892845 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH:15]=1)[CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:23]([O:16][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:15][C:12]=1[CH:13]=[O:14])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 149712582-Hydroxy-5-phenoxybenzaldehyde

Product 1

HCID 104477522-Benzyloxy-5-phenoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Phenoxy-2-hydroxybenzaldehyde (20 g, 94 mmol) and potassium carbonate (26.1 g, 188 mmol) are taken up in DMF (250 mL) and treated with benzyl bromide (16.1 g, 94 mmol). The mixture is stirred at room temperature overnight. The mixture is diluted with ethyl acetate and washed three times with saturated aqueous ammonium chloride, dried over magnesium sulfate and evaporated to give 2-benzyloxy-5-phenoxybenzaldehyde as a colorless solid. This is used without further purification.

Workup

  1. washwashed three times with saturated aqueous ammonium chloride
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-8867b9d0b3334aae9bbc167c1acc113c
Source dataset
uspto-grants-1992_06
Patent number
US05120758

Reaction notes

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