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

HRID 487997Notes

Reaction equation

HRID 487997 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1.N.[CH3:23]O>>[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([O:17][CH3:23])=[O:16])=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 1118Sulfuric AcidHCID 815682-(4-Methylphenyl)benzoic acid

Product 1

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

Procedure

6 g of sulfuric acid in 12 ml of methanol was added to 3.2 g of 2-(4-methylphenyl)benzoic acid [see A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)], and the mixture was heated under reflux for 8 hr. The refluxed solution was cooled, poured into ice water, weakly alkalified with aqueous ammonia and extracted with ether. The extract was dried over anhydrous magnesium sulfate. The dried extract was concentrated, and the residue was recrystallized from n-hexane to prepare 2.4 g of the title compound.

Workup

  1. temperature, 43, 1372 (1978)], and the mixture was heated
  2. temperatureunder reflux for 8 hr
  3. temperatureThe refluxed solution was cooled
  4. extractionextracted with ether
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. extractionThe dried extract
  7. concentrationwas concentrated
  8. customthe residue was recrystallized from n-hexane
  9. customto prepare 2.4 g of the title compound

Sources & evidence

ORD record
ord-30fe95baf52d47dfabb5b62dc303d1a2
Source dataset
uspto-grants-1994_03
Patent number
US05298518

Reaction notes

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