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

HRID 75145

Reaction equation

HRID 75145 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].[I-].[K+].CN([CH:21]=[O:22])C>CCOC(C)=O.O>[CH2:6]([O:22][C:21]1[CH:8]=[CH:9][C:2]([CH:10]=[O:13])=[CH:3][CH:4]=1)[C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium Carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 4-hydroxybenzaldehyde (28.2 g, 231 mmol), potassium carbonate (47.9 g, 35 mmol), potassium iodide and DMF(280 mL) benzyl bromide was added slowly at 0° C. The mixture was stirred at rt overnight. The mixture was diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with 1N aq HCl and dried. The solution was concentrated to give 4-benzyloxybenzaldehyde (46.5 g, 95%). 1H NMR: (CDCl3, 400 MHZ) δ=5.15 (s, 2H), 7.06 (m, 2H), 7.42(m, 5H), 7.84(m, 2H), 9.89(s, 1H).

Workup

  1. additionwas added slowly at 0° C
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with 1N aq HCl
  5. customdried
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-42ea015766b440f091058e5f05edbb7f
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Linked notes

Loading…