2-Hydroxy-4-vinyl-benzoic acid methyl ester → Methyl 4-ethyl-2-hydroxybenzoate

HRID 629470

Reaction equation

HRID 629470 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH:12]=[CH2:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>C(O)C.[C].[Pd]>[CH2:12]([C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=1)[CH3:13]

Participants

4

Reactant 1

HCID 200893762-Hydroxy-4-vinyl-benzoic acid methyl ester

Product 1

HCID 54092218Methyl 4-ethyl-2-hydroxybenzoateYield 61.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 2-hydroxy-4-vinylbenzoate (2.31 g) in ethanol (25.0 mL) was added palladium-carbon (1.38 g), and the mixture was stirred overnight at room temperature under hydrogen atmosphere. The insoluble substance was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.43 g).

Workup

  1. customThe insoluble substance was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dbf89bd7c938424387e80510ea411f7a
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Linked notes

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