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

HRID 2082183Notes

Reaction equation

HRID 2082183 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>[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 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 mole (40.0 g) of 4-hydroxybenzoic acid and 0.35 mole (30.9 g) of (S)-(-)-2-methylbutanol were refluxed for 20 hours in 150 ml of toluene in the presence of 1 ml of conc. sulfuric acid. The reaction solution was concentrated, and then purified by column chromatography to obtain 53.2 g of 4-hydroxybenzoic acid 2-methylbutyl ester [[α]D23 =+4.95* (CHCL3)]. (yield: 88%)

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-03f04eab193a45299a09aacfd575a4ce
Source dataset
uspto-grants-1993_02
Patent number
US05187298

Reaction notes

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