Benzyl Bromide → 4-Benzyloxy-2-methoxybenzaldehyde

HRID 471428

Reaction equation

HRID 471428 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 42939904-Benzyloxy-2-methoxybenzaldehydeYield 62.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxy-2-methoxybenzaldehyde (2.0 g, 13.15 mmol), benzyl bromide (3.14 mL, 26.3 mmol) and potassium carbonate (3.63 g, 26.3 mmol) are combined in acetone (5 mL) and the mixture is stirred for 4 hours. The mixture is concentrated under vacuum, suspended in dichloromethane and washed with water. The organic phase is concentrated under vacuum and the residue purified by flash chromatography (10% ethyl acetate in cyclohexane) to give the title compound (yield 2.0 g).

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. washwashed with water
  3. concentrationThe organic phase is concentrated under vacuum
  4. customthe residue purified by flash chromatography (10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-261053784076497a937144debb75293a
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Linked notes

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