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

HRID 2352589Notes

Reaction equation

HRID 2352589 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 water. The resulting reaction solution was then washed with water to remove sulfuric acid. The organic phase was then dried, concentrated, and purified by column chromatography to obtain 5.0 g of the objective ester (liquid, at room temperature, [α]D23 =+4.9° (CHCl3)). (Yield: 83%).

Workup

  1. customwhile removing water
  2. customThe resulting reaction solution
  3. washwas then washed with water
  4. customto remove sulfuric acid
  5. customThe organic phase was then dried
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-add7f219f9ef4ce3ad1a57efc1189a73
Source dataset
uspto-grants-1989_10
Patent number
US04877858

Reaction notes

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