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

HRID 2289864Notes

Reaction equation

HRID 2289864 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 pellets in 250 ml of water is stirred at 60° C. for 195 minutes. The solution is cooled to 10° C. and acidified to pH 5-6 with glacial acetic acid. The crystalline product is filtered off with suction, washed with 200 ml of water a little at a time and dried at 45° C. in a vacuum drying oven. 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. filtrationThe crystalline product is filtered off with suction
  2. washwashed with 200 ml of water a little at a time
  3. customdried at 45° C. in a vacuum
  4. customdrying oven

Sources & evidence

ORD record
ord-d628342f728144f09704fe72bbfa9fd8
Source dataset
uspto-grants-2000_07
Patent number
US06093837

Reaction notes

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