Oxalyl chloride → HCID 13281349, compound

HRID 1388828Notes

Reaction equation

HRID 1388828 reaction equation
[Cl:1][C:2]1[C:3]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH2:14][CH2:15][CH2:16][C:17]([Cl:23])=[O:19])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 132813484-(3-Chloro[1,1'-biphenyl]-2-yl)butanoic acid

Product 1

HCID 13281349HCID 13281349, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a dry argon atmosphere a stirred solution of 4-(3-chloro[1,1'-biphenyl]-2-yl)butanoic acid (22.8 g, 0.083 mole) in toluene (500 ml) was heated at 65°. Oxalyl chloride (21 g, 0.166 mole) was added slowly to the reaction mixture. After complete addition the mixture was allowed to stir at 40° for approximately 18 hours. The solvent and excess oxalyl chloride were removed by distillation under reduced pressure. Further distillation under reduced pressure gave 4-(3-chloro[1,1'-biphenyl]-2-yl)butanoic acid chloride (b.p. 150°/0.04 mm) as a clear oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionAfter complete addition the mixture
  2. customThe solvent and excess oxalyl chloride were removed by distillation under reduced pressure
  3. distillationFurther distillation under reduced pressure

Sources & evidence

ORD record
ord-eb3c7b76e98a4f35b2dd2d45c218a345
Source dataset
uspto-grants-1984_02
Patent number
US04433182

Reaction notes

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