Acetic Acid → (5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oxime

HRID 612805Notes

Reaction equation

HRID 612805 reaction equation
[OH-].[K+].[CH3:3][O:4][N:5]=[C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]1=[N:15][OH:16].[CH2:17]1[O:19][CH2:18]1.C(O)(=O)C>O>[CH3:3][O:4][N:5]=[C:6]([C:7]1[O:19][CH2:18][CH2:17][O:16][N:15]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[OH:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 14797Potassium HydroxideHCID 178502623HCID 178502623, compound

Product 1

HCID 136030529(5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oximeYield 41.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 20° C., 19.8 g (0.3 mol) of potassium hydroxide pellets are added to a suspension of 38.4 g (0.2 mol) of benzofuran-2,3-dione 3-(O-methyl-oxime) 2-oxime in 400 ml of water and the mixture was stirred for 30 minutes, on which a solution forms. At 20° C., 17.6 g (0.4 mol) of ethylene oxide are introduced over a period of 75 minutes, and the mixture is stirred at 20° C. overnight, on which a precipitate forms. The mixture is then stirred at 60° C. for 11 hours, on which the precipitate redissolves. The solution is cooled and acidified to pH 5-6 with glacial acetic acid. The crystalline product is filtered off with suction, washed with 300 ml of water a little at a time and dried at 45° C. in a vacuum drying cabinet. 19.6 g (39.3% of theory) of (5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oxime are obtained.

Workup

  1. stirringthe mixture is stirred at 20° C. overnight, on which a precipitate forms
  2. stirringThe mixture is then stirred at 60° C. for 11 hours, on which the precipitate
  3. dissolutionredissolves
  4. temperatureThe solution is cooled
  5. filtrationThe crystalline product is filtered off with suction
  6. washwashed with 300 ml of water a little at a time
  7. customdried at 45° C. in a vacuum
  8. customdrying cabinet

Sources & evidence

ORD record
ord-2b73b2d7dcc5471faca233124fb3b389
Source dataset
uspto-grants-1999_12
Patent number
US06005104

Reaction notes

Loading…