3-Hydroxybenzaldehyde → 3-Benzyloxybenzaldehyde

HRID 1267419Notes

Reaction equation

HRID 1267419 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.CCCCCC.C(OCC)(=O)C>[CH2:10]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7503Benzyl ChlorideHCID 10340Sodium Carbonate

Product 1

HCID 743423-BenzyloxybenzaldehydeYield 84%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

24.2 g (0.2 mol) of 3-hydroxybenzaldehyde and 25.32 g (0.2 mol) of benzyl chloride were placed in 500 ml of acetone and 21.2 g (0.2 mol) of sodium carbonate was added thereto. The resulting solution was stirred for 12 to 24 hours with heating, cooled to room temperature. The solvent was removed under a reduced pressure and the residue thus obtained was washed with water and the extracted with ethyl acetate twice. The organic layer was dried and the solvent was removed under a reduced pressure to obtain a residue. The residue was subjected to column chromatography using a mixture of n-hexane and ethyl acetate (9:1) as an eluent to obtain 35.6 g (yield 84%) of the title compound as a colorless liquid.

Workup

  1. temperaturewith heating
  2. customThe solvent was removed under a reduced pressure
  3. customthe residue thus obtained
  4. washwas washed with water
  5. extractionthe extracted with ethyl acetate twice
  6. customThe organic layer was dried
  7. customthe solvent was removed under a reduced pressure
  8. customto obtain a residue

Sources & evidence

ORD record
ord-5bcdeef5d1714f1986c8a6ef438b631b
Source dataset
uspto-grants-2003_04
Patent number
US06552080B1

Reaction notes

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