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

HRID 636845Notes

Reaction equation

HRID 636845 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]1=[N:13][O:14][CH2:15][CH2:16][OH:17].[OH-].[K+].C(O)(=O)C>O>[CH3:1][O:2]/[N:3]=[C:4](/[C:5]1[O:17][CH2:16][CH2:15][O:14][N:13]=1)\[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[OH:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 543010792,3-Benzofurandione, 2-[O-(2-hydroxyethyl)oxime] 3-(O-methyloxime)

Product 1

HCID 135542407Z-(5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oximeYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 25.6 g (0.1084 mol) of benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)oxime]3-(O-methyl oxime) and 14.2 g (0.216 mol) of potassium hydroxide lozenges in 250 ml of water is stirred at 60° C. for 195 minutes. The solution is cooled to 10° C. and acidified to a pH of 5-6 with glacial acetic acid. The product which has crystallized out is filtered off with suction, washed with 200 ml of water in portions and dried at 45° C. in a vacuum drying cabinet. 17.7 g (67.7% of theory) of E-(5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl oxime are obtained.

Workup

  1. customThe product which has crystallized out
  2. filtrationis filtered off with suction
  3. washwashed with 200 ml of water in portions
  4. customdried at 45° C. in a vacuum
  5. customdrying cabinet

Sources & evidence

ORD record
ord-7047b5d9da724c11a0659ab04e46d473
Source dataset
uspto-grants-2001_02
Patent number
US06194590B1

Reaction notes

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