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

HRID 1199864Notes

Reaction equation

HRID 1199864 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][C@@H: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 2723602(S)-2-methyl-1-butanol

Product 1

HCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.29 mol (40.0 g) of p-hydroxybenzoic acid and 0.35 mol (30.9 g) of (S)-(-)-2-methylbutanol were refluxed for 20 hours in 150 ml of toluene in the presence of 1 ml of concentrated sulfuric acid. The resulting reaction solution was concentrated and then purified by column chromatography to obtain 53.2 g of 2-methylbutyl p-hydroxybenzoate [[α]D23 =+4.95. (CHCl3)]

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-378dddc9a0df4669946d13c6b23f73d5
Source dataset
uspto-grants-1990_02
Patent number
US04904065

Reaction notes

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