Ethylene Glycol → HCID 21451192, compound

HRID 596266Notes

Reaction equation

HRID 596266 reaction equation
ClCCC[O:5][P:6]1[CH2:10][CH:9]=[C:8]([CH3:11])[CH2:7]1.[CH2:12](O)[CH2:13][OH:14].C(Br)C>ClCCCl>[OH:14][CH2:13][CH2:12][P:6]1(=[O:5])[CH2:10][CH2:9][C:8]([CH3:11])=[CH:7]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6332Ethyl BromideHCID 21451191HCID 21451191, compound

Product 1

HCID 21451192HCID 21451192, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 14.7 g. (0.076 mole) of 1-(chloropropoxy)-3-methyl-3-phospholene in 50 ml. of 1,2-dichloroethane was added, with stirring, over a period of 5 minutes, a total of 14.14 g. (0.23 mole) of ethylene glycol. The resulting solution was cloudy. Ethyl bromide (1.66 g.) was added and the mixture was heated under reflux for 1 hour. At the end of this time the solvent and other volatile materials were removed by evaporation and the residue was distilled under reduced pressure. There was thus obtained 1.3 g. (10.6% theoretical yield) of a mixture of the 2- and 3-isomers of 1-(2-hydroxyethyl)-3-methylphospholene-1-oxide in the form of a liquid having a boiling point of 125° - 150° C at 0.2 mm. of mercury. A glassy residue remained in the distillation flask and was believed to be 1,1'-ethylenebis-(3-methylphospholene-1-oxide).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customAt the end of this time the solvent and other volatile materials were removed by evaporation
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-6dcd1dcb515847499ef712ddd5664595
Source dataset
uspto-grants-1977_03
Patent number
US04010209

Reaction notes

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