Chloroethane → 4-Methoxyphenyl phenyl(2,4,6-trimethylbenzoyl)phosphinate

HRID 1440368Notes

Reaction equation

HRID 1440368 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4](Cl)=[O:5].[C:13]1([P:19]([O:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[O:20]CC)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)C>C(N(CC)CC)C>[C:13]1([P:19]([C:4](=[O:5])[C:3]2[C:2]([CH3:1])=[CH:10][C:9]([CH3:11])=[CH:8][C:7]=2[CH3:12])(=[O:20])[O:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6337Chloroethane2×HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 18983531HCID 18983531, compound

Product 1

HCID 189835024-Methoxyphenyl phenyl(2,4,6-trimethylbenzoyl)phosphinateYield 65%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

59.5 g (0.326 mol) of 2,4,6-trimethylbenzoyl chloride and 0.75 g of triethylamine were heated to 115° C. and 45 g (0.163 mol) of monoethyl mono-4-methoxyphenyl phenylphosphonite were added dropwise in one hour under a nitrogen atmosphere and with vigorous stirring. Ethyl chloride was given off as a gas and was condensed in a downstream cold trap. The mixture was then further stirred at 110° to 115° C. for 90 minutes. In total, at the end of the reaction, 9 g (88% of theory) of ethyl chloride were situated in the cold trap. The excess 2,4,6-trimethylbenzoyl chloride was then distilled off at 1 mbar and the residue was distilled with the aid of a thin-film evaporator (bath temperature: 260° C.; 0.4 mbar). 40 g were obtained. The yield was 65% of theory.

Workup

  1. customcondensed in a downstream cold trap
  2. distillationThe excess 2,4,6-trimethylbenzoyl chloride was then distilled off at 1 mbar
  3. distillationthe residue was distilled with the aid of a thin-film evaporator (bath temperature: 260° C.; 0.4 mbar)
  4. custom40 g were obtained

Sources & evidence

ORD record
ord-d90c133c02834fc3b9b52884046adf04
Source dataset
uspto-grants-1996_03
Patent number
US05498741

Reaction notes

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