Chloroethane → HCID 18983522, compound

HRID 1440370Notes

Reaction equation

HRID 1440370 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][CH:27]=[CH:26][C:25]=2[C:30]([CH3:33])([CH3:32])[CH3:31])[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:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([CH3:32])([CH3:31])[CH3:33])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6337Chloroethane2×HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 10935541HCID 10935541, compound

Product 1

HCID 18983522HCID 18983522, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

69.7 g (0.382 mol) of 2,4,6-trimethylbenzoyl chloride and 0.9 g of triethylamine were heated under a nitrogen atmosphere to 115° C. and 57.8 g (0.191 mol) of monoethyl mono-2-tert-butylphenyl phenylphosphonite were added dropwise in one hour with stirring. Ethyl chloride was given off as a gas and was condensed in a downstream cold trap. The mixture was further stirred for 2 hours. In total, 11.7 g of ethyl chloride (95% of theory) condensed. After distilling off the excess acid chloride, the residue was distilled with the aid of a thin-film evaporator (bath temperature: 270° C.; 0.4 mbar). 70 g were obtained. The product was brought to crystallization from concentrated acetone solution, melting point: 76°-79° C. The yield was 87% of theory.

Workup

  1. customcondensed in a downstream cold trap
  2. stirringThe mixture was further stirred for 2 hours
  3. distillationAfter distilling off the excess acid chloride
  4. distillationthe residue was distilled with the aid of a thin-film evaporator (bath temperature: 270° C.; 0.4 mbar)
  5. custom70 g were obtained
  6. customThe product was brought to crystallization from concentrated acetone solution, melting point: 76°-79° C

Sources & evidence

ORD record
ord-bec4990568654214ab7d93dfb6010d15
Source dataset
uspto-grants-1996_03
Patent number
US05498741

Reaction notes

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