Ethanolamine → HCID 54035625, compound

HRID 128161Notes

Reaction equation

HRID 128161 reaction equation
[CH3:1][CH:2]([CH3:13])[CH:3]([Cl:12])[CH2:4][C:5](Cl)([Cl:10])[C:6]([F:9])([F:8])[F:7].C(CN)O>CN(C)C=O>[Cl:10][C:5](=[CH:4][CH:3]([Cl:12])[CH:2]([CH3:1])[CH3:13])[C:6]([F:7])([F:8])[F:9]

Participants

4

Reactant 2

HCID 700Ethanolamine2×HCID 14350311HCID 14350311, compound

Product 1

HCID 54035625HCID 54035625, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
96 °C

Procedure

A mixture comprising 5-methyl-2,2,4-trichoro-1,1,1-trifluorohexane (51.5 g), monoethanolamine (6.1 g), cuprous chloride (0.1 g) and dimethylformamide (100 ml) is stirred and heated at 96° C. (internal temperature) under a nitrogen atmosphere. When the initial green colour of the mixture is discharged further aliquots of monoethanolamine are added until a geen colour persists and GLC analysis shows that the starting material has been consumed. The reaction is complete after 5 hours. The crude product is isolated by precipitation with water, extraction with dichloromethane and removal of the solvent under reduced pressure. Distillation affords 2,4-dichloro-5-methyl-1,1,1,trifluorohex-2-ene (71%), b.p. 79°-82° C./100 mm Hg; 'Hnmr (CDCl3)τ9.2-8.8 (q, 6H); 8.2-7.8 (m, H); 5.6-5.3 (m, H); 3.9-3.4 (pair of doublets, H).

Workup

  1. additionare added until a geen colour persists and GLC analysis
  2. customhas been consumed
  3. customThe crude product is isolated by precipitation with water, extraction with dichloromethane and removal of the solvent under reduced pressure
  4. distillationDistillation

Sources & evidence

ORD record
ord-303f5cdf99e44839b02e3087c07c49ec
Source dataset
uspto-grants-1981_03
Patent number
US04259263

Reaction notes

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