Ethanol → [5-(1H-Imidazol-1-yl)-2-methylphenyl](2,4,6-trimethylphenyl)methanol

HRID 543325Notes

Reaction equation

HRID 543325 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:15][C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])=[O:5].C(O)C.[BH4-].[Na+]>O>[CH3:12][C:11]1[CH:10]=[C:9]([CH3:13])[CH:8]=[C:7]([CH3:14])[C:6]=1[CH:4]([C:3]1[CH:15]=[C:16]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH:17]=[CH:18][C:2]=1[CH3:1])[OH:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 20206223HCID 20206223, compound

Product 1

HCID 145956[5-(1H-Imidazol-1-yl)-2-methylphenyl](2,4,6-trimethylphenyl)methanolYield 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 7.3 g of 2-methyl-5-(1-imidazolyl)-2',4',6'-trimethylbenzophenone is 50 ml of ethanol is added a solution of 1 g of sodium borohydride in 10 ml of water. After the mixture is stirred at 50° C. for 10 hours, the reaction mixture is poured into ice-cold water. The crystals precipitated are filtered off and recrystallized from ethanol to give 5.8 g of α-(2,4,6-trimethylphenyl)-2-methyl-5-(1-imidazolyl)benzenemethanol as white crystals, melting at 190°-191° C.

Workup

  1. additionthe reaction mixture is poured into ice-cold water
  2. customThe crystals precipitated
  3. filtrationare filtered off
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-56b083c9984746b9b7bcd6cd79507ed5
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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