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

HRID 1919749Notes

Reaction equation

HRID 1919749 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

A 10% palladium-carbon catalyst (608 mg) was added to a mixed solution of methyl 4-hydroxy-3-(2-propen-1-yl)benzoate (12.16 g, 0.63 mol) in methanol (50 mL), followed by hydrogenation overnight. The catalyst was separated from the reaction solution by filtration, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 10.83 g of the title compound (yield: 88%) as a colorless powder.

Workup

  1. customThe catalyst was separated from the reaction solution by filtration
  2. concentrationfollowed by concentration under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-81c71c4361164565842eae309029f1d8
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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