Carbon Tetrachloride → (1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

HRID 1681377Notes

Reaction equation

HRID 1681377 reaction equation
BrN1[C:6](=O)[CH2:5][CH2:4][C:3]1=O.N(C(C)(C)C#N)=N[C:11](C)(C)[C:12]#N.C[C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:23]=1[C:24]([OH:26])=[O:25].[C:32](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:3][C:4]1[CH:12]=[CH:11][C:31]([C:27]2[C:23]([C:24]([O:26][CH3:32])=[O:25])=[CH:22][CH:30]=[CH:29][CH:28]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 124392,6-Dimethylbenzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 1393873(1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (19.6 g) and azo(bisisobutyronitrile) (200 mg) were added to a solution of 2,6-dimethylbenzoic acid in carbon tetrachloride (300 ml) and chloroform (50 ml). The mixture was degassed, placed under an atmosphere of argon and then heated under reflux for 2 hours. The mixture was cooled to ambient temperature and insoluble material removed by filtration. The filtrate was then extracted with aqueous sodium bicarbonate solution and the aqueous extracts carefully acidified with 48% hydrobromic acid. The precipitated solid was collected by filtration and dried under vacuum to give 4-bromomethyl-2-methylbenzoic acid (B) (3.92 g) as a white solid, m.p. 157°-160° C.; NMR (CDCl3): 2.66(s, 3H), 4.56(s, 2H), 7.2-7.35(complex m, 2H), 8.04(d, 1H).

Workup

  1. customThe mixture was degassed
  2. temperatureheated
  3. temperatureunder reflux for 2 hours
  4. custominsoluble material removed by filtration
  5. extractionThe filtrate was then extracted with aqueous sodium bicarbonate solution
  6. filtrationThe precipitated solid was collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-72bb49c0fd3348d48f086f238cf6115f
Source dataset
uspto-grants-1992_12
Patent number
US05171748

Reaction notes

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