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

HRID 1388827Notes

Reaction equation

HRID 1388827 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-d11ba302c3b04be6a081ad09d76f00dd
Source dataset
uspto-grants-1984_02
Patent number
US04433182

Reaction notes

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