Glycol monoethyl ether → HCID 101835019, compound

HRID 2287011Notes

Reaction equation

HRID 2287011 reaction equation
[Na].[H-].[Na+:3].Cl[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:14]([O-:17])(=[O:16])=[O:15].[Na+].[CH3:19][CH2:20][O:21][CH2:22][CH2:23][OH:24]>>[CH2:20]([O:21][CH2:22][CH2:23][O:24][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:14]([O-:17])(=[O:16])=[O:15])[CH3:19].[Na+:3]

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 24758Sodium hydrideHCID 70350Benzenesulfonic acid, 2-chloro-5-nitro-, sodium salt (1:1)HCID 5360545Sodium

Product 1

HCID 101835019HCID 101835019, compound

Procedure

To a solution of sodium 2-ethoxyethylate prepared by adding 7.3 g of sodium hydride (14.6 g of a 50% suspension in liquid paraffin) to 300 ml of ethyl Cellosolve, was added 55 g of sodium 2-chloro-5-nitrobenzenesulfonate. The reaction mixture was heated at 80° to 85° C. with stirring for 30 minutes. After completion of the reaction, the insoluble materials were removed by filtration and from the filtrate 150 ml of ethyl Cellosolve was distilled off under reduced pressure. To the concentrated solution was added 300 ml of isopropyl alcohol and the mixture was cooled with ice. The crystals thus-precipitated were recovered by filtration, washed with 100 ml of isopropyl alcohol and air-dried. Yield: 33 g; Melting Point: 248° to 249° C.

Workup

  1. temperatureThe reaction mixture was heated at 80° to 85° C.
  2. customAfter completion of the reaction
  3. customthe insoluble materials were removed by filtration and from the filtrate 150 ml of ethyl Cellosolve
  4. distillationwas distilled off under reduced pressure
  5. additionTo the concentrated solution was added 300 ml of isopropyl alcohol
  6. temperaturethe mixture was cooled with ice
  7. customThe crystals thus-precipitated
  8. filtrationwere recovered by filtration
  9. washwashed with 100 ml of isopropyl alcohol
  10. customair-dried

Sources & evidence

ORD record
ord-82a6472f3b144a269ae95e6fec102083
Source dataset
uspto-grants-1981_05
Patent number
US04268625

Reaction notes

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