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

HRID 482811Notes

Reaction equation

HRID 482811 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>C1C=CC=CC=1>[CH3:11][CH:12]([CH2:15][CH3:16])[CH2:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

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

Product 1

HCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

690 g of p-hydroxybenzoic acid, 650 g of (-)2-methylbutanol, 3 l of benzene, and 30 ml of conc. sulfuric acid were stirred under heating in a container provided with a Dean-Stark reflux condenser to remove generated water. After the reflux for about 11 hours, the solution was cooled and stripped of sulfuric acid by the addition of ice water. The reaction mother liquor was distilled of benzene after being washed by an aqueous solution of sodium carbonate and water to obtain oily p-hydroxybenzoic acid 2-methylbutyl ester.

Workup

  1. temperatureunder heating in a container
  2. customprovided with a Dean-Stark
  3. temperaturereflux condenser
  4. customto remove
  5. temperatureAfter the reflux for about 11 hours
  6. temperaturethe solution was cooled
  7. additionstripped of sulfuric acid by the addition of ice water
  8. distillationThe reaction mother liquor was distilled of benzene
  9. washafter being washed by an aqueous solution of sodium carbonate and water

Sources & evidence

ORD record
ord-21108a6732094ae0ade2a04382afcf0c
Source dataset
uspto-grants-1986_03
Patent number
US04576732

Reaction notes

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