Citric Acid → (1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol

HRID 928447Notes

Reaction equation

HRID 928447 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](OC)=[O:12])=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:15].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CC(=O)OCC>C1COCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:15]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 62649Sodium sulfate decahydrateHCID 21998749Methyl 1,2-dimethyl-1H-benzimidazole-5-carboxylate

Product 1

HCID 2998315(1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Methyl 1,2-dimethyl-1H-benzo[d]imidazole-5-carboxylate (500 mg, 2.448 mmol) in THF (24.5 ml) Lithiumaluminium hydride (1 M in THF, 2.44 ml) was added at 0° C. After 2 hours sodium sulfate decahydrate and citric acid was added to the reaction to destroy the excess of lithiumaluminiumhydride. After 1 hour, methanol (25 ml) was added and the fine suspension was filtered off. The filtrate was evaporated under reduced pressure to afford a brown solid. EA (50 ml) was added and the suspension was treated in an ultra sonic bath. The solid was filtered off and this procedure was repeated twice. The yellow filtrate was evaporated under reduced pressure to afford crude (1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol.

Workup

  1. customto destroy the excess of lithiumaluminiumhydride
  2. additionmethanol (25 ml) was added
  3. filtrationthe fine suspension was filtered off
  4. customThe filtrate was evaporated under reduced pressure
  5. customto afford a brown solid
  6. additionthe suspension was treated in an ultra sonic bath
  7. filtrationThe solid was filtered off
  8. customThe yellow filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7018b9a92df343af9db66a8f7dd2e912
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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