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

HRID 709406Notes

Reaction equation

HRID 709406 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium Carbonate (678 g, 4.91 mol) was added to a solution of 4-hydroxybenzaldehyde (200 g, 1.63 mol) in DMF (2 L) followed to the addition of benzyl bromide (214 mL, 1.80 mol) at 0° C. and stirred for 18 h at RT. After completion, the reaction mixture was poured into ice water (3 L), filtered the solid and dried to get 4-(benzyloxy)benzaldehyde (230 g, 66%).

Workup

  1. filtrationfiltered the solid
  2. customdried

Sources & evidence

ORD record
ord-e600cdd3b7354abb8bdb2ada39feab1c
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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