Methyl 4-(1H-imidazol-1-yl)benzoate → (4-(1H-Imidazol-1-yl)phenyl)methanol

HRID 1591185Notes

Reaction equation

HRID 1591185 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1COCC1>[OH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2766374Methyl 4-(1H-imidazol-1-yl)benzoateHCID 68718528lithium aluminium hydride THF

Product 1

HCID 2776486(4-(1H-Imidazol-1-yl)phenyl)methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(1H-imidazol-1-yl)benzoic acid methyl ester (prepared as described in U.S. Pat. No. 4,804,662) (1.5 g) in THF (25 ml) at -15° C. was added a solution of 1M LAH/THF (10.4) ml). The mixture was stirred for 1/2 hour and allowed to warm to room temperature. The reaction was quenched by addition of water (0.5 ml), and then diluted with methanol (50 ml) and filtered. Concentration of the filtrate yielded 1.2 g (98%) of 1-(hydroxymethyl)-4-(1H-imidazol-1-yl)-benzene.

Workup

  1. customprepared
  2. customThe reaction was quenched by addition of water (0.5 ml)
  3. additiondiluted with methanol (50 ml)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e56f5f2907b2490091a16fcf4ff92c47
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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