HCID 12659681, compound → HCID 23330247, compound

HRID 224756Notes

Reaction equation

HRID 224756 reaction equation
Cl[C:2]1([CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])[C:5]2([CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:9]>[Zn].C(O)=O>[Cl:12][C:11]([Cl:13])([Cl:14])[CH2:10][CH:2]1[C:5]2([CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:9]

Participants

4

Reactant 1

HCID 12659681HCID 12659681, compound

Product 1

HCID 23330247HCID 23330247, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
30 °C

Procedure

18 g of 1-chloro-1-(2',2',2'-trichloroethyl)spiro(3.3)-heptan-2-one is placed into 200 ml of formic acid, and 8.5 g of zinc dust is added portionwise in such a way that the temperature does not exceed 30° C. The reaction mixture is afterwards stirred for two hours at 30° C. and then filtered. The filtrate is concentrated by evaporation; water is added and the mixture is extracted with diethyl ether. The ethereal phase is washed with water, with aqueous sodium carbonate solution and again with water; it is dried over sodium sulphate and concentrated by evaporation. The residue is distilled at 75°-80° C./0.03-0.05 Torr to yield 1-(2',2',2'-trichloroethyl)spiro(3.3)heptan-2-one of the formula ##STR12## as a clear liquid.

Workup

  1. additionis added portionwise in such a way that the temperature
  2. customdoes not exceed 30° C
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated by evaporation
  5. additionwater is added
  6. extractionthe mixture is extracted with diethyl ether
  7. washThe ethereal phase is washed with water, with aqueous sodium carbonate solution and again with water
  8. dry with materialit is dried over sodium sulphate
  9. concentrationconcentrated by evaporation
  10. distillationThe residue is distilled at 75°-80° C./0.03-0.05 Torr

Sources & evidence

ORD record
ord-72e98eebb13e4708b445c7d36ab84950
Source dataset
uspto-grants-1980_11
Patent number
US04234517

Reaction notes

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