Sodium Hydroxide → alpha-(2,6-Dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanol

HRID 543333Notes

Reaction equation

HRID 543333 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:17][C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]([OH:15])=[O:14])=[CH:8][C:7]=1[CH3:16])=[O:5].[OH-].[Na+].[BH4-].[Na+]>O>[CH3:16][C:7]1[CH:8]=[C:9]([C:13]([OH:15])=[O:14])[CH:10]=[C:11]([CH3:12])[C:6]=1[CH:4]([C:3]1[CH:17]=[C:18]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:19]=[CH:20][C:2]=1[Cl:1])[OH:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 202062352-Chloro-5-(1-imidazolyl)-2',6'-dimethyl-4'-carboxybenzophenone

Product 1

HCID 13851129alpha-(2,6-Dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanolYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6.4 g of 2-chloro-5-(1-imidazolyl)- 2',6'-dimethyl-4'-carboxybenzophenone and 0.8 g of sodium hydroxide in 35 ml of water is added 1.4 g of sodium borohydride, and the mixture is stirred at 70°-75° C. for 3 hours. After completion of the reaction, a small amount of an insoluble substance is filtered off from the warm mixture and the filtrate is adjusted to pH 4 with concentrated hydrochloric acid under stirring at 80°-90° C. The precipitated crystals are collected by filtration under reduced pressure, washed with water and acetone and dried to give 6.1 g of α-(2,6-dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanol, melting at 317°-320° C. with decomposition as white crystals.

Workup

  1. customAfter completion of the reaction
  2. filtrationa small amount of an insoluble substance is filtered off from the warm mixture
  3. stirringunder stirring at 80°-90° C
  4. filtrationThe precipitated crystals are collected by filtration under reduced pressure
  5. washwashed with water and acetone
  6. customdried

Sources & evidence

ORD record
ord-e5dd576a9d034743b80497a2979a9425
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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