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

HRID 1430188Notes

Reaction equation

HRID 1430188 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, 8, (0.615 g, 2.22 mmol) in THF (20 mL) and H2O (5 mL) at room temperature 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 and dried to afford 0.532 g (91%) of the desired product 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
  7. customdried

Sources & evidence

ORD record
ord-f27f132f7a5844fc9a6713e2de89a1a6
Source dataset
uspto-grants-2015_01
Patent number
US08940773B2

Reaction notes

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