Ethylene Oxide → 2,3-Benzofurandione, 2-[O-(2-hydroxyethyl)oxime] 3-(O-methyloxime)

HRID 1250015Notes

Reaction equation

HRID 1250015 reaction equation
[CH2:1]1[O:3][CH2:2]1.[CH3:4][O:5][N:6]=[C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]1=[N:16][OH:17].[OH-].[Na+]>O>[CH3:4][O:5][N:6]=[C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]1=[N:16][O:17][CH2:1][CH2:2][OH:3]

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 14798Sodium HydroxideHCID 178502623HCID 178502623, compound

Product 1

HCID 543010792,3-Benzofurandione, 2-[O-(2-hydroxyethyl)oxime] 3-(O-methyloxime)Yield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

At 20° C., 264.3 g (6.0 mol) of ethylene oxide are passed into a solution of 192.2 g (1.0 mol) of benzofuran-2,3-dione 3-(O-methyl-oxime) 2-oxime in 2 l of water over a period of 85 minutes. The solution is cooled to 5° C. and 70 g (1.06 mol) of sodium hydroxide pellets are added, on which the temperature increases to 10° C. The mixture is stirred without further cooling for another 165 minutes and the precipitate that has formed is filtered off with suction, washed with 500 ml of ice-water a little at a time and dried at 40° C. in a vacuum drying cabinet. 143.0 g (61% of theory) of benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)-oxime]3-(O-methyl-oxime) are obtained as a mixture of two stereoisomers.

Workup

  1. temperatureincreases to 10° C
  2. temperaturewithout further cooling for another 165 minutes
  3. customthe precipitate that has formed
  4. filtrationis filtered off with suction
  5. washwashed with 500 ml of ice-water a little at a time
  6. customdried at 40° C. in a vacuum
  7. customdrying cabinet

Sources & evidence

ORD record
ord-2bf3cfb6e8534564a8e64a0883f2b04c
Source dataset
uspto-grants-2002_01
Patent number
US06335454B1

Reaction notes

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