Acetic Acid → 5-phenylhexanoic Acid

HRID 840969Notes

Reaction equation

HRID 840969 reaction equation
[CH3:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8]CC)=[O:7].S(=O)(=O)(O)O.C(O)(=O)C>O>[CH3:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 22620530Ethyl 5-methyl-5-phenylpentanoate

Product 1

HCID 27556195-phenylhexanoic AcidYield 0.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-methyl-5-phenylpentanoate (16.0 g, 72.6 mmol), a 30% aqueous sulfuric acid solution and acetic acid (250 ml) was stirred at 75-80° C. for 6 hours. The reaction mixture was poured into cold water and extracted twice with toluene, and the extract solution was washed twice with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 13.4 mg of 5-methyl-5-phenylpentanoic acid.

Workup

  1. extractionextracted twice with toluene
  2. washthe extract solution was washed twice with a 5% aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f09dcd769f98497f98f52eab5903c66a
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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