Hydrochloric Acid → 4-Benzyloxy-3-hydroxybenzaldehyde

HRID 1713293Notes

Reaction equation

HRID 1713293 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C)C=O>[CH2:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[OH:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3,4-dihydroxybenzaldehyde (21.6 g), potassium carbonate (21.56 g) and N,N-dimethylformamide (200 mL) was added dropwise benzyl bromide (18.5 mL) under ice-cooling, and the resulting mixture was stirred at room temperature for 16 hours. Two mol/L hydrochloric acid (40 mL) was added to the reaction mixture and the whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (19.0 g).

Workup

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-d9a0300ce0ab4135bf2308f8331e7391
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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