4-Hydroxybenzoic Acid → 3-Methylpentyl p-hydroxybenzoate

HRID 6317

Reaction equation

HRID 6317 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]([CH2:16][CH3:17])[CH2:13][CH2:14]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][CH2:14][CH2:13][CH:12]([CH3:11])[CH2:16][CH3:17])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 641003(S)-(+)-3-Methyl-1-pentanol

Product 1

HCID 190183233-Methylpentyl p-hydroxybenzoateYield 80.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.7 g of p-hydroxybenzoic acid and 11.4 g of (S)-(+)-3-methyl-1-pentanol were refluxed for 10 hours in toluene in the presence of sulfuric acid, while removing out the generated water from the reaction system. Subsequently, the reaction solution was washed with water to remove the sulfuric acid out. The reaction solution was then dried, concentrated, and purified by column chromatography, to obtain 17.8 g of the objective ester compound (liquid state at room temperature ([α]D23 =+7.8° (CHCl3)). (Yield: 80%)

Workup

  1. customwhile removing out the generated water from the reaction system
  2. washSubsequently, the reaction solution was washed with water
  3. customto remove the sulfuric acid out
  4. customThe reaction solution was then dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-9ad13e2b1c894f9687888c893b7a5b06
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Linked notes

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