Benzyl Bromide → 4-Benzyloxy-3-ethyl-5-methylbenzaldehyde

HRID 1676129Notes

Reaction equation

HRID 1676129 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17])[CH:12]=[O:13])[CH3:8].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:17][C:16]1[C:15]([CH3:18])=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][C:9]=1[CH2:7][CH3:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 231592103-Ethyl-4-hydroxy-5-methylbenzaldehyde

Product 1

HCID 866393484-Benzyloxy-3-ethyl-5-methylbenzaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of K2CO3 (21 g, 152 mmol) in acetone (200 mL), 3-ethyl-4-hydroxy-5-methyl-benzaldehyde (5.0 g, 30.5 mmol) followed by benzyl bromide (7.87 g, 45.7 mmol) is added. The suspension is refluxed for 16 h before it is filtered. The filtrate is concetrated and the crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (5.04 g) as colourless oil; LC-MS: tR=1.09 min, [M+1]+=255.25.

Workup

  1. additionis added
  2. temperatureThe suspension is refluxed for 16 h before it
  3. filtrationis filtered
  4. customthe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-67cf4c848417464b9f0ffd0245e92743
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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