Water → 2-(4-Hydroxyphenoxy)-3-methylquinoxaline

HRID 64582

Reaction equation

HRID 64582 reaction equation
C([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[C:23]([CH3:24])=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.O>C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]2[C:23]([CH3:24])=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 962WaterHCID 136705372-(4-Benzyloxyphenoxy)-3-methylquinoxaline

Product 1

HCID 136705382-(4-Hydroxyphenoxy)-3-methylquinoxalineYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 12.5 g (0.05 mole) borontribromide in 100 cc methylene chloride was added, over a period of 40 minutes, to a well stirred, cold (-62° C.) solution of 17.1 g 2-(4-benzyloxyphenoxy)-3-methylquinoxaline (0.05 mole) in 400 cc methylene chloride. When the addition was complete, the temperature of the reaction was allowed to rise slowly (2 hours) to room temperature. The reaction mixture was then poured into 1 liter of water and an additional 500 cc of methylene chloride was added. The mixture was stirred vigorously for 40 minutes and the insoluble solid was filtered. Crystallization from an ethanol-water mixture (1:1) gave 6.4 g of product, m.p. 175°-178° C.

Workup

  1. additionWhen the addition
  2. custom(2 hours)
  3. customto room temperature
  4. stirringThe mixture was stirred vigorously for 40 minutes
  5. filtrationthe insoluble solid was filtered
  6. customCrystallization from an ethanol-water mixture (1:1)

Sources & evidence

ORD record
ord-2e50a64fef51404880287fa09ec46d4f
Source dataset
uspto-grants-1986_09
Patent number
US04609396

Linked notes

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