Sodium Hydroxide → 6-Cyano-4,4-diphenylhexanoic acid

HRID 1781503Notes

Reaction equation

HRID 1781503 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([CH2:3][CH2:4][C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:6][CH2:7][C:8]([OH:10])=[O:9])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19610260Ethyl 6-cyano-4,4-diphenylhexanoate

Product 1

HCID 190455936-Cyano-4,4-diphenylhexanoic acidYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 6-cyano-4,4-diphenylhexanoate (25.5 g) in ethanol (400 ml) was added 1N-aqueous sodium hydroxide solution (120 ml) and the mixture was heated and stirred at 60° C. for 1 hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the group was made acidic to with 1N-hydrochloric acid and extracted with ethyl acetate (200 ml×2). The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to dryness. The group (25 g) was recrystallized from chloroform-hexane to provide the title compound (22 g) as white powder.

Workup

  1. temperaturethe mixture was heated
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate (200 ml×2)
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe group (25 g) was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-c45ce467eda245a8a90c7c579be52209
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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