Potassium Hydroxide → 3,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid

HRID 1884696Notes

Reaction equation

HRID 1884696 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:8]([O:18][CH2:19][CH2:20][OH:21])=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH:6]=1)C.[OH-].[K+]>C1COCC1.CCO>[Cl:17][C:13]1[CH:12]=[C:11]([C:9]2[CH:10]=[C:5]([CH:6]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:8]=2[O:18][CH2:19][CH2:20][OH:21])[C:4]([OH:29])=[O:3])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 539906423,5-Bis-(m-chlorophenyl)4-(2-hydroxyethoxy)benzoic acid ethyl ester

Product 1

HCID 222373953,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of 3,5-bis-(m-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid ethyl ester (0.620 g, 1.44 mmol) in THF:EtOH (3:2, 30 mL) at room temperature was added 1 N KOH (7.20 mL, 7.20 mmol) dropwise. After 18 h at this temperature, the reaction mixture was concentrated and diluted with H2O (100 mL). The aqueous solution was acidified to pH 1 with 2 N HCl. The solid [3,5-bis-(m-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid] that formed was filtered off, washed with excess H2O, and then dried on the high vacuum pump (0.450 g, 78%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with H2O (100 mL)

Sources & evidence

ORD record
ord-222557d9b2994c8386b5ef0cf532ed6d
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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