4-Carbobenzoxyoxybenzoic acid 1-methylbutyl ester → Pentan-2-YL 4-hydroxybenzoate

HRID 231024Notes

Reaction equation

HRID 231024 reaction equation
[CH3:1][CH:2]([O:6][C:7](=[O:25])[C:8]1[CH:13]=[CH:12][C:11]([O:14]C(OCC2C=CC=CC=2)=O)=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH3:5].[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH3:1][CH:2]([O:6][C:7](=[O:25])[C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 542047674-Carbobenzoxyoxybenzoic acid 1-methylbutyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 19365293Pentan-2-YL 4-hydroxybenzoateYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 10 m moles of the above 4-carbobenzoxyoxybenzoic acid 1-methylbutyl ester, 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 and purified by column chromatography to obtain 1.9 g of 4-hydroxybenzoic acid 1-methylbutyl ester. (yield: 89%)

Workup

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

Sources & evidence

ORD record
ord-98774643b5724ebf8331924e0ee59645
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Reaction notes

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