Acetone → Methyl 3-(benzyloxy)-5-hydroxybenzoate

HRID 1670073Notes

Reaction equation

HRID 1670073 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+].C(Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C)=[O:27]>>[CH3:1][O:2][C:3](=[O:10])[C:4]1[CH:5]=[C:6]([OH:27])[CH:7]=[C:8]([O:14][CH2:11][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 87647Methyl cyclohex-1-ene-1-carboxylate

Product 1

HCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoateYield 40%

Procedure

3,5-Dihydrobenzoic acid methyl ester (20.2 g) was dissolved in acetone (400 mL) and then potassium carbonate (16.6 g) and benzyl bromide (20.5 g) were added. The resulting mixture was refluxed for 3 h. Then the insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified on a silica gel column using chloroform and methanol to yield 12.4 g (40% yield) of the title compound.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 h
  2. filtrationThen the insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-299e7a503e9f433dbbbc34f2ef9c3541
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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