Vanillin → 4-(Benzyloxy)-3-methoxybenzaldehyde

HRID 2186530Notes

Reaction equation

HRID 2186530 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:24][C:21]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-methoxy-4-hydroxy benzaldehyde (10.0 g; 64.9 mmol) in dry acetone (80 ml), potassium carbonate (17.9 gm, 129.8 mmol) and BnBr (11.5 ml, 97.30 mmol) were added and stirred in room temperature for 18 hours. Potassium carbonate was filtered, acetone concentrated and the residue purified on silica gel to give the title compound as a crystalline solid 14 gm, 88%). 1H NMR (CDCl3, 200 MHz): δ 3.9 (s, 3H), 5.2 (s, 2H), 6.95 (d, J=8.37 HZ, 1H), 7.4 (m, 7H), 9.8 (s, 1H); Mass (m/z): M+242, mp: 58° C.

Workup

  1. filtrationPotassium carbonate was filtered
  2. concentrationacetone concentrated
  3. customthe residue purified on silica gel

Sources & evidence

ORD record
ord-45a54cd3e0b4455bb6c8b77c44c072b2
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

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