Diketene → HCID 13718265, compound

HRID 851449Notes

Reaction equation

HRID 851449 reaction equation
[CH3:1][PH:2]([O-:17])([O-:16])[O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C=[C:19]1[O:23][C:21](=[O:22])[CH2:20]1.[CH2:24](P(C)([O-])([O-])[O-])CCCCCCCCCCC>>[O:22]=[C:21]1[CH2:20][CH:19]([CH2:1][P:2](=[O:16])([O:17][CH3:24])[O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[O:23]1

Participants

4

Reactant 3

HCID 12661DiketeneHCID 131712988HCID 131712988, compoundHCID 178443311HCID 178443311, compound

Product 1

HCID 13718265HCID 13718265, compound

Conditions

Temperature
85 °C

Procedure

A mixture of 13.2 parts of dodecyl methylphosphite, 4.2 parts of diketene and 0.6 parts of bis-(t-butylcyclohexyl)-perdicarbonate was added dropwise over 30 minutes to 39.6 parts of dodecylmethylphosphite which was vigorously stirred at 85° C. in a nitrogen atmosphere. On completion of the addition the reaction mixture was heated for a further 30 minutes at 85° C., then the excess of dodecylmethylphosphite was removed on a wiped wall still at a wall temperature of 80° C. and pressure 0.013 mb. The residue was distilled on a wiped wall still at a wall temperature of 150° C. and pressure 0.013 mb, and gave dodecyl methyl 2-oxo-4-oxetanylmethylphosphonate as a colourless oil which had the following analysis by weight:

Workup

  1. additionOn completion of the addition the reaction mixture
  2. temperaturewas heated for a further 30 minutes at 85° C.
  3. customthe excess of dodecylmethylphosphite was removed on a wiped wall still at a wall temperature of 80° C. and pressure 0.013 mb
  4. distillationThe residue was distilled on a wiped wall still at a wall temperature of 150° C. and pressure 0.013 mb

Sources & evidence

ORD record
ord-4bfb9e8ee5ac41ad868210490865445c
Source dataset
uspto-grants-1983_05
Patent number
US04384966

Reaction notes

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