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

HRID 1666588Notes

Reaction equation

HRID 1666588 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[CH:6]=[O:7])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:11][C:10]1[C:9]([CH3:12])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:1][CH3:2])[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 73.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-ethyl-4-hydroxy-5-methyl-benzaldehyde (8.00 g, 48.7 mmol) in acetone (130 mL), K2CO3 (20.2 g, 146.2 mmol) followed by benzylbromide (12.5 g, 73.1 mmol) is added. The suspension is stirred at reflux for 16 h before it is filtered and the solvent of the filtrate is removed in vacuo. The residue is separated by CC on silica gel to give 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (9.07 g) as a pale yellow oil; LC-MS: tR=1.09 min, [M+1]+=255.08.

Workup

  1. additionis added
  2. temperatureat reflux for 16 h before it
  3. filtrationis filtered
  4. customthe solvent of the filtrate is removed in vacuo
  5. customThe residue is separated by CC on silica gel

Sources & evidence

ORD record
ord-9227861861ea4721af7554b752c562fa
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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