Hydrochloric Acid → 4-(3-Chloro[1,1'-biphenyl]-2-yl)butanoic acid

HRID 544683Notes

Reaction equation

HRID 544683 reaction equation
Cl[C:2]1([CH2:14][CH2:15][CH2:16][C:17]#N)[CH2:7][CH:6]=[CH:5][CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-:19].[K+].[ClH:21].[Cl-].[Na+].[OH2:24]>C(O)CO>[Cl:21][C:7]1[C:2]([CH2:14][CH2:15][CH2:16][C:17]([OH:24])=[O:19])=[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 70490311HCID 70490311, compound

Product 1

HCID 132813484-(3-Chloro[1,1'-biphenyl]-2-yl)butanoic acid

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A stirred solution of 4-(2-chloro[1,1'-biphenyl]-2-yl)butanenitrile (2.7 g, 0.011 mole), potassium hydroxide (6.9 g, 0.11 mole), and ethylene glycol (25 ml) in water (25 ml) was heated at reflux for approximately 18 hours. The reaction mixture was cooled to room temperature, diluted with ice water (100 g) and acidified with concentrated hydrochloric acid. The mixture was saturated with sodium chloride, then extracted with diethyl ether (three 100 ml portions) and methylene chloride (100 ml). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to yield 4-(3-chloro[1,1'-biphenyl]-2-yl)butanoic acid as a solid (m.p. 74°-76°).

Workup

  1. temperatureat reflux for approximately 18 hours
  2. extractionextracted with diethyl ether (three 100 ml portions) and methylene chloride (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-92e3423034954ade82003a2de9cd0f0f
Source dataset
uspto-grants-1984_05
Patent number
US04451484

Reaction notes

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