8-(2,2,2-Trifluoroethylidene)-1,4-dioxaspiro[4.5]decane → 4-(2,2,2-Trifluoroethyl)cyclohexanone

HRID 1530797Notes

Reaction equation

HRID 1530797 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]=[C:4]1[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1.[H][H]>C(O)C.[Pd]>[F:1][C:2]([F:14])([F:15])[CH2:3][CH:4]1[CH2:5][CH2:6][C:7](=[O:8])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 212526788-(2,2,2-Trifluoroethylidene)-1,4-dioxaspiro[4.5]decaneHCID 178418361HCID 178418361, compound

Product 1

HCID 212526664-(2,2,2-Trifluoroethyl)cyclohexanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

At atmospheric pressure, 22.0 g of 8-(2,2,2-trifluoroethylidene)-1,4-dioxaspiro[4.5]decane in 250 ml of ethanol were hydrogenated in the presence of palladium on carbon as catalyst until no further uptake of hydrogen was visible. The catalyst was subsequently filtered off and the filtrate was concentrated. The residue was taken up in 170 ml of formic acid and stirred at 20° C. to 25° C. for 4 h. The reaction solution was poured into water, adjusted to pH 8 with potassium carbonate and extracted with methylene chloride. The combined organic phases were dried with magnesium sulfate and concentrated to give the title product as a colourless oil which was reacted further without any purification.

Workup

  1. filtrationThe catalyst was subsequently filtered off
  2. concentrationthe filtrate was concentrated
  3. additionThe reaction solution was poured into water
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic phases were dried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a4b2fe19bcfa49e9bf3c7a90543be261
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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