Benzoyl Peroxide → HCID 13718271, compound

HRID 851453Notes

Reaction equation

HRID 851453 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:25]1([P:31]([O-:35])[O:32][CH2:33][CH3:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:33]([O:32][P:31]([CH2:1][CH:2]1[O:6][C:4](=[O:5])[CH2:3]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 12661DiketeneHCID 18981701ethoxy(phenyl)phosphinite2×

Product 1

HCID 13718271HCID 13718271, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 8.4 parts of diketene, 2.5 parts of benzoyl peroxide and 20.0 parts of ethyl phenylphosponite were added dropwise over 1 hr to 48.1 parts of vigorously stirred ethyl phenylphosphonite which was heated at 120° C. in an atmosphere of nitrogen. The excess phosphonite was removed by passing the reaction mixture down a wiped wall still at 80° C. at a pressure of 0.013 mb. The residue was distilled on a wiped wall still at a temperature of 110° C. and a pressure of 0.013 mb and the product, ethyl(2-oxo-4-oxetanylmethyl)phenylphosphinate, was obtained as a colourless oil which was shown by 31P NMR to be a nearly equal mixture of diastereoisomers having chemical shifts at δ-37.5 and δ-37.7 and which had the following elemental analysis by weight.

Workup

  1. customThe excess phosphonite was removed
  2. customstill at 80° C.
  3. distillationThe residue was distilled on a wiped wall still at a temperature of 110° C.

Sources & evidence

ORD record
ord-b9c40b02ba8a486dabc075d540ffea18
Source dataset
uspto-grants-1983_05
Patent number
US04384966

Reaction notes

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