HCID 13656998, compound → HCID 14675642, compound

HRID 358733Notes

Reaction equation

HRID 358733 reaction equation
Cl[C:2]([F:18])([F:17])[C:3](Cl)([F:15])[CH2:4][CH:5]([Cl:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CC(O)C.[Zn]>[Cl:14][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:4][C:3]([F:15])=[C:2]([F:17])[F:18]

Participants

4

Reactant 1

HCID 13656998HCID 13656998, compound

Product 1

HCID 14675642HCID 14675642, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3776IsopropanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A stirred suspension of 2.1 grams (0.033 mole) of zinc dust in 100 ml of 1-methylethanol is heated to 100° C. and a solution of 10.0 grams (0.030 mole) of 1,2,4-trichloro-1,1,2-trifluorododecane in 50 ml of 1-methylethanol is added dropwise. Upon completion of addition, the reaction mixture is heated at 100° C. for 60 hours. The reaction mixture is cooled to ambient temperature and filtered. The filtrate is concentrated under reduced pressure to a residual oil. The oil is fractionally distilled under reduced pressure through a Vigreux column. The appropriate fractions are combined to yield 4.0 grams of 4-chloro-1,1,2-trifluoro-1-dodecene; b.p. 70°-73° C./0.5mm. The nmr spectrum is consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture is heated at 100° C. for 60 hours
  3. temperatureThe reaction mixture is cooled to ambient temperature
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure to a residual oil
  6. distillationThe oil is fractionally distilled under reduced pressure through a Vigreux column

Sources & evidence

ORD record
ord-10a02b01543d45a9bc1f7be24b9bbe28
Source dataset
uspto-grants-1991_03
Patent number
US04997855

Reaction notes

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