Methane → HCID 178519558, compound

HRID 1194388Notes

Reaction equation

HRID 1194388 reaction equation
CC1(C)[O:7][C:6]2[C:8]([CH2:12][C:13]3[N:14]=[CH:15][NH:16][CH:17]=3)=[CH:9][CH:10]=[CH:11][C:5]=2[CH2:4][O:3]1.Cl.C>O>[NH:16]1[CH:17]=[C:13]([CH2:12][C:8]2[C:6]([OH:7])=[C:5]([CH2:4][OH:3])[CH:11]=[CH:10][CH:9]=2)[N:14]=[CH:15]1

Participants

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 178431335HCID 178431335, compound

Product 1

HCID 178519558HCID 178519558, compoundYield 804.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

82.83 g (0.0339 mole) of 4-[(2,2-dimethyl-4H-1,3-benzodioxin-8-yl)methyl]-1H-imidazole (prepared in Example 5.2.) are suspended in 1645 ml of water (pH 7.9) and dissolved by the addition, over the course of 80 minutes, of 349 ml of a 1N aqueous solution of hydrochloric acid. When this addition is complete, the pH of the solution is 2.5. The reaction mixture is subsequently heated for 1 hour on an oil bath at 120° C. The solution is then cooled, treated with 5 g of Norit and filtered on Hyflo-cel. The solution is subsequently rendered alkaline by the addition of 242.5 ml of a 1N aqueous solution of sodium hydroxide (pH 8.5). The precipitate obtained is filtered off, washed with water and dried. This precipitate is then dissolved in 3.3 liters of ethyl acetate in the presence of Norit and of a few grams of sodium sulfate. The mixture is then filtered, concentrated to a volume of 400 ml and left to crystrallize. There are obtained 55.67 g of 3-[(1H-imidazol-4-yl)methyl]-2-hydroxybenzenemethanol. Yield: 80.4% of theory; M.P.: 152°-155° C.

Workup

  1. additionWhen this addition
  2. temperatureThe solution is then cooled
  3. filtrationfiltered on Hyflo-cel
  4. additionby the addition of 242.5 ml of a 1N aqueous solution of sodium hydroxide (pH 8.5)
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. washwashed with water
  8. customdried
  9. dissolutionThis precipitate is then dissolved in 3.3 liters of ethyl acetate in the presence of Norit and of a few grams of sodium sulfate
  10. filtrationThe mixture is then filtered
  11. concentrationconcentrated to a volume of 400 ml
  12. waitleft

Sources & evidence

ORD record
ord-14592daf941f40ba95bbd937410caa97
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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