Vanillin → 4-(Benzyloxy)-3-methoxybenzaldehyde

HRID 1616783Notes

Reaction equation

HRID 1616783 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:9]=[CH:10][C:11]1[CH:19]=[CH:18][C:16]([OH:17])=[C:13]([O:14][CH3:15])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:17][C:16]1[CH:18]=[CH:19][C:11]([CH:10]=[O:9])=[CH:12][C:13]=1[O:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1183VanillinHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (1.2 mL, 9.9 mmol) was added to a suspension of vanillin (1.0 g, 6.6 mmol) and potassium carbonate (2.7 g, 20 mmol) in acetone (10 mL) and treated according to Procedure 3. The crude product was recrystallised from EtOH to give 4-benzyloxy-3-methoxybenzaldehyde (1.0 g, 64%) as a colourless crystalline solid; mp 61-62° C.; δH (400 MHz, CDCl3) 3.95 (s, 3H, OCH3), 5.25 (s, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.32-7.45 (m, 7H, H2, H6, Ph), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 56.1, 70.8 109.3, 112.4, 126.6 127.2, 128.2, 128.7, 130.3, 136.0, 150.1, 153.6, 190.9; vmax 988, 1133, 1259, 1505, 1583, 1672 cm−1.

Workup

  1. additiontreated
  2. customThe crude product was recrystallised from EtOH

Sources & evidence

ORD record
ord-cc21dd38f3634747859c9545faffe734
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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