2-Butyne-1,4-diol → HCID 21451197, compound

HRID 596268Notes

Reaction equation

HRID 596268 reaction equation
ClCCC[O:5][P:6]1[CH2:10][CH:9]=[C:8]([CH3:11])[CH2:7]1.[CH2:12](O)[C:13]#[C:14][CH2:15][OH:16].P1CCCC=1>ClCCCl>[OH:16][CH2:15][C:14]([P:6]1(=[O:5])[CH2:10][CH:9]=[C:8]([CH3:11])[CH2:7]1)=[C:13]=[CH2:12]

Participants

5

Reactant 3

HCID 80662-Butyne-1,4-diolHCID 21451191HCID 21451191, compoundHCID 22639555HCID 22639555, compound2×

Product 1

HCID 21451197HCID 21451197, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A total of 14.3 g. (0.08 mole) of 1-(chloropropoxy)-3-methyl-3-phospholene was added in two halves to a suspension of 6.8 g. (0.08 mole) of 2-butyn-1,4-diol in 25 ml. of 1,2-dichloroethane. The second half of the phospholene was added dropwise after the slow exotherm, generated by the first addition, had subsided. The maximum temperature reached in the first exotherm was 45° C and, in the second exotherm, was 60° C. After the addition of all phospholene was complete, the mixture was stirred for 30 minutes without heating and then was heated under reflux for 30 minutes. At the end of this time the solvent was removed by distillation and the residue was distilled in vacuo. There was thus obtained 1-(1-hydroxymethylallenyl)-3-methyl-3-phospholene-1-oxide in the form of a liquid.

Workup

  1. additiongenerated by the first addition
  2. customwas 45° C and, in the second exotherm
  3. customwas 60° C
  4. temperaturewithout heating
  5. temperaturewas heated
  6. temperatureunder reflux for 30 minutes
  7. customAt the end of this time the solvent was removed by distillation
  8. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-73dd8fe8b0ce46d1bf09f1ddfb8024cf
Source dataset
uspto-grants-1977_03
Patent number
US04010209

Reaction notes

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