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

HRID 1033701Notes

Reaction equation

HRID 1033701 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C1C=CC=CC=1>[CH3:6][CH:5]([CH2:4][CH3:3])[CH2:9][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric Acid

Product 1

HCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl esterYield 64.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To p-hydroxybenzoic acid (113 g, 0.82 mol) were added S(-)-2-methyl-butanol (273 g, 3.1 mols), conc. sulfuric acid (25 ml) and benzene (300 ml), followed by refluxing the mixture for 16 hours, cooling, thereafter adding toluene (1 l), washing the toluene layer with 2% NaHCO3 aqueous solution and further with water till the washing water became neutral, distilling off toluene and recrystallizing from ethanol to obtain optically active p-hydroxy-benzoic acid 2-methyl-butyl ester (55 g).

Workup

  1. temperatureby refluxing the mixture for 16 hours
  2. temperaturecooling
  3. washadding toluene (1 l), washing the toluene layer with 2% NaHCO3 aqueous solution
  4. distillationdistilling off toluene
  5. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-13001d2788f646ba93f8f324b9bc2f15
Source dataset
uspto-grants-1994_05
Patent number
US05312564

Reaction notes

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