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

HRID 75840

Reaction equation

HRID 75840 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+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=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)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 4-Hydroxy benzaldehyde (10 g) in acetone (200 ml), potassium carbonate (16.96 g) was added and stirred. To this, benzyl bromide (12.67 ml) was added and the reaction mixture was refluxed for 3 hours and then cooled. The reaction mixture was filtered and the filtrate was concentrated to obtain pale brown colored oil which got solidified at room temperature. Solid was crystallized from DCM-Petroleum ether to obtain the title compound as pale yellow solid. Yield: 13 g (74%); 1HNMR (CDCl3; 300 MHz): δ 9.91 (s, 1H), 7.87 (d, 2H), 7.33-7.43 (m, 5H), 7.12 (d, 21-1) 5.17 (s, 2H).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. temperaturecooled
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customto obtain pale brown colored oil which
  6. customgot solidified at room temperature
  7. customSolid was crystallized from DCM-Petroleum ether

Sources & evidence

ORD record
ord-4d56e7fd93da410b8bd0ac4a0d464ab6
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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