Hydrochloric Acid → 2',4'-Dichloro-biphenyl-4-carboxylic acid

HRID 227888Notes

Reaction equation

HRID 227888 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1.CO>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 102657054-(2,4-Dichlorophenyl)-benzoic acid methyl ester

Product 1

HCID 107542792',4'-Dichloro-biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2′,4′-Dichloro-biphenyl-4-carboxylic acid methyl ester (3 g) was dissolved in a mixture of THF (25 mL) and methanol (25 mL). 1 M NaOH (50 mL) was added and the mixture stirred for 4 hours by which stage a clear solution had formed. Conc. HCl was added and the precipitate was collected as a white solid. Toluene was added and the mixture was evaporated to dryness to give the title compound as a white solid. 1H NMR (CDCl3): δ 7.20 (2H, m), 7.52 (2H, m), 7.64 (1H, s) and 8.12 (2H, m).

Workup

  1. customhad formed
  2. customthe precipitate was collected as a white solid
  3. additionToluene was added
  4. customthe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-bf9ed09c7c234c0083f56ea99fa2a9d6
Source dataset
uspto-grants-2009_07
Patent number
US07560597B2

Reaction notes

Loading…