Water → 4-(4-Chlorophenyl)-2-methoxybenzoic acid

HRID 2188537Notes

Reaction equation

HRID 2188537 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][CH:12]=2)=[CH:7][C:6]=1[O:18][CH3:19])=[O:4].O.[Li+].[OH-]>C1COCC1>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[C:6]([O:18][CH3:19])[CH:7]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 595130824'-Chloro-3-methoxy-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 248911994-(4-Chlorophenyl)-2-methoxybenzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-chloro-3-methoxy-biphenyl-4-carboxylic acid methyl ester, 30, (0.615 g, 2.22 mmol) in THF (20 mL) and H2O (5 mL) is added LiOH (0.932 g, 22.2 mmol). The resulting suspension is heated to reflux for 2 hours. The reaction is cooled and concentrated under reduced pressure. The crude product is acidified using conc. HCl and the resulting solid is collected by filtration, washed with H2O to afford 0.532 g (91% yield) of the desired compound as a grey solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.69 (1H, br s), 8.26 (1H, d, J=8.1 Hz), 7.53-7.58 (2H, m), 7.44-7.50 (2H, m), 7.33 (1H, dd, J=8.1, 1.6 Hz), 7.20 (1H, d, J=1.3 Hz), 4.17 (3H, s). HPLC-MS: m/z 263 [M+H]+.

Workup

  1. temperatureThe resulting suspension is heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction is cooled
  4. concentrationconcentrated under reduced pressure
  5. filtrationthe resulting solid is collected by filtration
  6. washwashed with H2O

Sources & evidence

ORD record
ord-b65dd98d09304d329a6bee4db114f73d
Source dataset
uspto-grants-2012_12
Patent number
US08323671B2

Reaction notes

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