Diethylene Glycol Monoethyl Ether → HCID 20186289, compound

HRID 2309280Notes

Reaction equation

HRID 2309280 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])[CH3:6]>N1C=CC=CC=1>[Cl-:3].[CH2:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])[CH3:6]

Participants

4

Reactant 2

HCID 8146Diethylene Glycol Monoethyl EtherHCID 24386Thionyl Chloride

Product 1

HCID 20186289HCID 20186289, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

487 ml of thionyl chloride are added dropwise to a stirred solution of 805 g of diethylene glycol monoethyl ether in 10 ml of pyridine. After all has been added, the mixture is heated to 80°. The initially vigorous evolution of gas ceases after about 3 hours. The reaction mixture is then degassed in vacuo, affording as residue 843 g of diethylene glycol monoethyl ether chloride which is taken up in 1 l of ethanol and stirred with 750 ml of ammonia in an autoclave at 130° for 15 hours. After cooling, 240 g of sodium hydroxide are cautiously added. The mixture is filtered and the residue is washed with alcohol. The filtrate is concentrated by evaporation and the residue is dried by azeotropic distillation with toluene and then purified by fractional distillation through a Vigreux column. The main fraction, diethylene glycolamine ethyl ether, distills at 73°-76°/17 mbar. Yield: 382 g (48% of theory).

Workup

  1. additionAfter all has been added
  2. temperaturethe mixture is heated to 80°
  3. customThe reaction mixture is then degassed in vacuo

Sources & evidence

ORD record
ord-36f6105be76b4e389f2d18c3915d20d6
Source dataset
uspto-grants-1987_09
Patent number
US04694105

Reaction notes

Loading…