Hydrochloric Acid → 3-Methyl-5-phenylpentanoic acid

HRID 840976Notes

Reaction equation

HRID 840976 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([CH3:16])[CH2:10][C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CO.Cl>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH:9]([CH3:16])[CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 563065Ethyl 5-phenyl-3-methylpentanoate

Product 1

HCID 135704873-Methyl-5-phenylpentanoic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-phenyl-3-methylpentanoate (0.30 g, 1.36 mmol), a 1N-aqueous sodium hydroxide solution (3 ml), methanol (3 ml) and tetrahydrofuran (3 ml) was stirred at room temperature for 5 hours. The reaction mixture was adjusted to pH 1 with a 1N-aqueous hydrochloric acid solution and extracted with ethyl acetate. The extract solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.24 g of 5-phenyl-3-methylpentanoic acid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract solution was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bf170e5914d0428e9876121304eddf81
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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