Hydrochloric Acid → HCID 13345032, compound

HRID 224758Notes

Reaction equation

HRID 224758 reaction equation
Cl.Cl[C:3]([Cl:15])([Cl:14])[CH2:4][CH:5]1[O:12][C:11](=[O:13])[CH2:10][C:6]21[CH2:9][CH2:8][CH2:7]2.CC[O-].[Na+].[OH-].[Na+]>C(O)C>[Cl:15][C:3]([Cl:14])=[CH:4][CH:5]1[C:6]2([CH2:7][CH2:8][CH2:9]2)[CH:10]1[C:11]([OH:12])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723922Sodium ethoxideHCID 23330249HCID 23330249, compound

Product 1

HCID 13345032HCID 13345032, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Dry HCl is introduced into 2.57 g (0.01 mol) of the 5-(2',2',2'-trichloroethyl)-6-oxaspiro(3.4)-octan-7-one, produced according to Example 11, in 30 ml of absolute ethanol. After the reaction has subsided (temperature rise up to 55° C.), the reaction mixture is concentrated by evaporation; it is then taken up in absolute ethanol, and 0.011 mol of sodium ethylate (produced from 0.27 g of sodium in ethanol) is added. After a stirring period of 30 minutes, the mixture is concentrated by evaporation; 38 ml (about 0.06 mol) of 10% sodium hydroxide solution is added, and stirring is maintained at 95° C. for 6 hours. After cooling, the mixture is washed with several portions of diethyl ether, acidified with sulphuric acid, and extracted with diethyl ether. The ether extracts after drying over sodium sulphate are concentrated by evaporation. By filtration of the residue from the ten-fold amount by weight of silica gel (eluant: hexane/diethyl ether in the volume ratio of 1:1), a small amount of strongly polar impurities is removed. After concentration of the filtrate by evaporation, there is obtained 2-(2',2'-dichlorovinyl)spiro(2.3)hexane-1-carboxylic acid of the formula ##STR15## having a melting point of 122°-128° C.

Workup

  1. customproduced
  2. custom(temperature rise up to 55° C.)
  3. concentrationthe reaction mixture is concentrated by evaporation
  4. concentrationthe mixture is concentrated by evaporation
  5. temperatureAfter cooling
  6. washthe mixture is washed with several portions of diethyl ether
  7. extractionextracted with diethyl ether
  8. dry with materialafter drying over sodium sulphate
  9. concentrationare concentrated by evaporation
  10. filtrationBy filtration of the residue from the ten-fold amount by weight of silica gel (eluant
  11. customhexane/diethyl ether in the volume ratio of 1:1), a small amount of strongly polar impurities is removed
  12. customAfter concentration of the filtrate by evaporation

Sources & evidence

ORD record
ord-53242c0dbd944c40b4bf8cf93e401943
Source dataset
uspto-grants-1980_11
Patent number
US04234517

Reaction notes

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