Isobutylene → 1,1,1-Trifluoro-4-methyl-2-(trifluoromethyl)pent-4-en-2-ol

HRID 1727449Notes

Reaction equation

HRID 1727449 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([C:5]([F:8])([F:7])[F:6])=[O:4].[CH3:11][C:12](=[CH2:14])[CH3:13].C(=O)=O.CC(O)C>>[F:1][C:2]([F:10])([F:9])[C:3]([C:5]([F:8])([F:7])[F:6])([OH:4])[CH2:13][C:12]([CH3:14])=[CH2:11]

Participants

4

Reactant 3

HCID 8255Isobutylene2×HCID 12695HexafluoroacetoneHCID 86586944Isopropanol carbon dioxide

Product 1

HCID 124203301,1,1-Trifluoro-4-methyl-2-(trifluoromethyl)pent-4-en-2-olYield 83%

Conditions

Temperature
20 °C

Procedure

Hexafluoroacetone (238 g) and 120 g of isobutylene were condensed into a lecture bottle using Dry Ice/2-propanol cooling. The temperature was raised in the sealed vessel to 20° C. while stirring in a water bath and temperature maintained overnight. The next morning the temperature was raised to 50° C. for 2 hours. After cooling, excess isobutylene was bled off and the product distilled at 100-115° C. to afford 264 g (83%) of a clear liquid. The identity of the product was confirmed using 1H NMR spectroscopy and HRMS.

Workup

  1. customcondensed into a lecture bottle
  2. temperaturetemperature maintained overnight
  3. temperatureThe next morning the temperature was raised to 50° C. for 2 hours
  4. temperatureAfter cooling
  5. distillationthe product distilled at 100-115° C.

Sources & evidence

ORD record
ord-a582c78cb5344403a4bf1063d1af903b
Source dataset
uspto-grants-2009_02
Patent number
US07495135B2

Reaction notes

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