Methyl 3-allyl-4-hydroxybenzoate → Methyl 4-hydroxy-3-propylbenzoate

HRID 1690134Notes

Reaction equation

HRID 1690134 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH:13]=[CH2:14]>[C].[Pd].CO>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 1

HCID 939882Methyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 11805593Methyl 4-hydroxy-3-propylbenzoateYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixed solution of methyl 4-hydroxy-3-(2-propen-1-yl)benzoate (12.16 g, 0.63 mol) and methanol (50 mL), 10% palladium carbon catalyst (608 mg) was added, and the mixture was stirred overnight under a hydrogen atmosphere. The catalyst was separated by filtration from the reaction solution which was then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (10.83 g, yield 88%) was obtained as a colorless powder.

Workup

  1. customThe catalyst was separated by filtration from the reaction solution which
  2. concentrationwas then concentrated in vacuo
  3. customThe obtained residue was purified

Sources & evidence

ORD record
ord-05ccd69ee4214de98131c41ecff21c85
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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