4-Carbobenzoxyoxybenzoic acid 1-methylpropyl ester → 2-Butyl p-hydroxybenzoate

HRID 2072649Notes

Reaction equation

HRID 2072649 reaction equation
[CH3:1][CH:2]([O:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([O:13]C(OCC2C=CC=CC=2)=O)=[CH:9][CH:8]=1)[CH2:3][CH3:4].[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH3:1][CH:2]([O:5][C:6](=[O:24])[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 542393354-Carbobenzoxyoxybenzoic acid 1-methylpropyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 866072-Butyl p-hydroxybenzoateYield 92.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 10 m moles (3.1 g) of the above 4-carbobenzoxyoxybenzoic acid 1-methylpropyl ester and 0.5 g of palladium carbon (5% catalyst) in 40 ml of ethyl acetate was reacted for four hours in an atmosphere of hydrogen gas. After the reaction, palladium carbon was filtered out using a membrane filter, and the filtrate was concentrated, then purified by column chromatography to obtain 1.7 g of 4-hydroxybenzoic acid 1-methylpropyl ester. (yield: 86%)

Workup

  1. filtrationwas filtered out
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-067df69a0dbb4cb39bd4fbbae227380f
Source dataset
uspto-grants-1990_04
Patent number
US04913839

Reaction notes

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