Hydrochloric Acid → 4-n-propylphenylacetic acid

HRID 2405652Notes

Reaction equation

HRID 2405652 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[CH:6][CH:5]=1)[CH2:2][CH3:3].Cl.S([O-])([O-])(=O)=[O:15].[Mg+2].[OH-:20].[Na+]>>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:15])=[O:20])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Procedure

2-(4-propylphenyl)acetonitrile (41.0 mg, 0.257 mmol) was dissolved in 1 mL of 30% aqueous sodium hydroxide solution and stirred under reflux condition for 4 hours. Upon completion of the reaction, the reaction solution was acidified by adding 3 mL of 10% aqueous hydrogen chloride solution and extracted with diethyl ether (3 mL×3). The organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 34.8 mg (0.195 mmol, 76%) of the desired compound (balance unit of tag β).

Workup

  1. temperatureunder reflux condition for 4 hours
  2. customUpon completion of the reaction
  3. extractionextracted with diethyl ether (3 mL×3)
  4. customThe organic layer thus obtained
  5. customto remove water
  6. filtrationThe precipitate was filtered out
  7. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-05bbc437b4c344b78edfc8230fa8f191
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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