Methanol → 5,5-diphenylpentanoic Acid

HRID 565653Notes

Reaction equation

HRID 565653 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH2:10][C:11]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:19].[Na+].C[OH:22]>O>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH2:10][C:11]([OH:22])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 137771625,5-Diphenylvaleronitrile

Product 1

HCID 109996075,5-diphenylpentanoic AcidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5,5-diphenylvaleronitrile (6.5 g) in methanol (30 mL), 80 mL of water and 10 g of sodium hydroxide were added, and the mixture was refluxed for 72 hours. After the reaction mixture was allowed to cool, it was washed with diethyl ether and adjusted to pH 1 with concentrated hydrochloric acid. This acidic solution was extracted with diethyl ether and the extract was washed with saturated aqueous NaCl, dried over MgSO4, and concentrated. The residue was recrystallized to provide 5.5 g of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 72 hours
  2. temperatureto cool
  3. washit was washed with diethyl ether
  4. extractionThis acidic solution was extracted with diethyl ether
  5. washthe extract was washed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was recrystallized

Sources & evidence

ORD record
ord-2a830033f0354345b80acafa67a07323
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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