4-Hydroxybenzoic Acid → Benzoic acid, 4-hydroxy-, 2-methylbutyl ester

HRID 6318

Reaction equation

HRID 6318 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][CH:12]([CH2:15][CH3:16])[CH2:13]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][CH:12]([CH3:13])[CH2:15][CH3:16])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 87232-Methyl-1-butanol

Product 1

HCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.0 g of p-hydroxybenzoic acid and 12.5 g of (-)-2-methylbutanol were refluxed for 6 hours in toluene in the presence of sulfuric acid, while removing the generated water out from the reaction system. Subsequently, the reaction solution was washed with water to remove sulfuric acid out. The reaction solution was then dried and concentrated, and the concentrate was purified by column chromatography, to obtain 5.0 g of the objective ester compound (liquid state at room temperature, [α]D23 =4.9° (CHCl3)). (Yield: 83%)

Workup

  1. customwhile removing the generated water out from the reaction system
  2. washSubsequently, the reaction solution was washed with water
  3. customto remove sulfuric acid out
  4. customThe reaction solution was then dried
  5. concentrationconcentrated
  6. customthe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-b4a0964d88644cb69fc49099e36ac464
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Linked notes

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