Diketene → HCID 13718273, compound

HRID 851451Notes

Reaction equation

HRID 851451 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]1([P:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[O:5]=[C:4]1[CH2:3][CH:2]([CH2:1][P:13](=[O:14])([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 608527Phosphinous acid, diphenyl-

Product 1

HCID 13718273HCID 13718273, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4.2 parts of diketene, 10.1 parts of diphenylphosphinous acid, 2.3 parts of bis-(t-butylcyclohexyl)-perdicarbonate and 70 parts of toluene was stirred by a stream of nitrogen in a quartz apparatus at room temperature while being irradiated by UV light from a medium pressure mercury lamp. After three hours irradiation, the reaction mixture was filtered, and the filtrate evaporated. The semi-crystalline residue was triturated with a little toluene, and the crystals collected on a filter and washed with toluene. Crystallisation from toluene gave colourless crystals of (2-oxo-4-oxetanylmethyl)-diphenylphosphine oxide which melted at 154°-155° C. and had the following elemental analysis by weight.

Workup

  1. customwhile being irradiated by UV light from a medium pressure mercury lamp
  2. customAfter three hours irradiation
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate evaporated
  5. customThe semi-crystalline residue was triturated with a little toluene
  6. customthe crystals collected on
  7. filtrationa filter
  8. washwashed with toluene
  9. customCrystallisation from toluene

Sources & evidence

ORD record
ord-8a60d77e6b40439db1ae29c68ec4db06
Source dataset
uspto-grants-1983_05
Patent number
US04384966

Reaction notes

Loading…