Vanillin → 4-(Benzyloxy)-3-methoxybenzaldehyde

HRID 1709848Notes

Reaction equation

HRID 1709848 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeYield 92.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-hydroxy-3-methoxybenzaldehyde (100.0 g, 0.657 mole), benzyl bromide (112.4 g, 0.657 mole), and potassium carbonate (90.8 g, 0.657 mole) was heated overnight at reflux in 600 ml of dry acetonitrile (dried over 4A molecular sieves). The reaction mixture was stripped to dryness on a rotary evaporator. A white solid was obtained which was recrystallized form ethanol and dried in vacuo overnight at 80° C., to give 147.45 g (92.6% yield) of white crystalline product, mp 58°-63° C.

Workup

  1. temperaturewas heated overnight
  2. customThe reaction mixture was stripped to dryness on a rotary evaporator
  3. customA white solid was obtained which
  4. customwas recrystallized form ethanol
  5. customdried in vacuo overnight at 80° C.

Sources & evidence

ORD record
ord-ec882d7b60c94963b1fd9aef5fa1f52e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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