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

HRID 2309426Notes

Reaction equation

HRID 2309426 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>CN(C=O)C.[Cl-].[Na+].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

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of p-hydroxybenzaldehyde (3.66 g, 30 mmole) in dry DMF (20 ml) was stirred with anhydrous potassium carbonate (12.5 g, 90 mmole) and benzylbromide (6.16 g, 36 mmole) was added. After 18 hours, the mixture was diluted with brine (75 ml) and extracted three times with ether. The extracts were combined, washed with dilute brine, dried over anhydrous magnesium sulfate and evaporated in vacuo to afford a solid. Crystallization from ethyl ether in hexane gave 5 g of title E compound as light yellow flakes, with consistent spectral data.

Workup

  1. additionwas added
  2. extractionextracted three times with ether
  3. washwashed with dilute brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customto afford a solid
  7. customCrystallization from ethyl ether in hexane
  8. customgave 5 g of title E compound as light yellow flakes

Sources & evidence

ORD record
ord-396adbcd24b6460589ad1f9b8830da35
Source dataset
uspto-grants-1987_09
Patent number
US04695585

Reaction notes

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