Ethanol → HCID 11644617, compound

HRID 1171887Notes

Reaction equation

HRID 1171887 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH2:14]CC#N)[CH:3]=1.[OH-:18].[Na+].[CH2:20]([OH:22])[CH3:21]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH2:14][CH2:21][C:20]([OH:18])=[O:22])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 11506992HCID 11506992, compound

Product 1

HCID 11644617HCID 11644617, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture composed of 280 mg (1.16 mmol) of 3-(4-chlorobiphenyl-2-yl)propanenitrile prepared in Example 53, 138 mg (3.475 mmol) of NaOH, 4 ml of ethanol and 4 ml water is refluxed for 6 hours. After cooling, the ethanol is concentrated under vacuum. 16 ml of water are then added and the mixture is washed with ethyl ether (2×20 ml), followed by acidification of the aqueous phase with 16% HCl. The resulting mixture is extracted with dichloromethane and the extracts are then dried over sodium sulfate. After concentrating the organic phase under vacuum, an oil is obtained, which crystallises after stirring in pentane, to give 171 mg of a white solid.

Workup

  1. temperatureis refluxed for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe ethanol is concentrated under vacuum
  4. addition16 ml of water are then added
  5. washthe mixture is washed with ethyl ether (2×20 ml)
  6. extractionThe resulting mixture is extracted with dichloromethane
  7. dry with materialthe extracts are then dried over sodium sulfate
  8. concentrationAfter concentrating the organic phase under vacuum
  9. customan oil is obtained
  10. customwhich crystallises

Sources & evidence

ORD record
ord-8d08b3d7c13a4e05aa2ea42f9d723729
Source dataset
uspto-grants-2010_11
Patent number
US07829721B2

Reaction notes

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