Benzyl Bromide → 2-Benzyloxy-4-isopropylbenzaldehyde

HRID 733346Notes

Reaction equation

HRID 733346 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 101490244-Isopropyl salicylaldehyde

Product 1

HCID 178562862-Benzyloxy-4-isopropylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-isopropylbenzaldehyde (6.69 g) and 11.26 g of potassium carbonate were suspended with 100 mL of N,N-dimethylformamide, and 5.33 mL of benzyl bromide was added to the stirred mixture at room temperature. After the mixture was stirred at room temperature for 16 hours, the insoluble material was removed by filtration. To the filtrate were added 10 mL of water and 10 mL of diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. After being washed with brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 10.44 g of 2-benzyloxy-4-isopropylbenzaldehyde.

Workup

  1. additionwas added to the stirred mixture at room temperature
  2. customthe insoluble material was removed by filtration
  3. additionTo the filtrate were added 10 mL of water and 10 mL of diluted hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. washAfter being washed with brine
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-f8b7c2827ce448b7a65df907c396b106
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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