Water → HCID 23108395, compound

HRID 1270609Notes

Reaction equation

HRID 1270609 reaction equation
[OH:1][C:2]1([C:9]([F:18])([F:17])[C:10](O)([OH:15])[C:11]([F:14])([F:13])[F:12])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.O>C1(C)C=CC=CC=1>[OH:1][C:2]1([C:9]([F:17])([F:18])[C:10](=[O:15])[C:11]([F:13])([F:14])[F:12])[CH2:3][CH2:4][C:5](=[O:8])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 962WaterHCID 23108399HCID 23108399, compound

Product 1

HCID 23108395HCID 23108395, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 80 ml of toluene was dissolved 10.0 g of 4-hydroxy-4-(2,2-dihydroxy-1,1,3,3,3-pentafluoropropyl)cyclohexanone obtained in <7-1>. The solution was heated under reflux. The water formed was removed, leaving a toluene solution of 4-hydroxy-4-(2-oxo-1,1,3,3,3-pentafluoropropyl)cyclohexanone. Under nitrogen and with stirring at room temperature, this solution was added dropwise to a solution of 3.3 g lithium aluminum hydride in 100 ml tetrahydrofuran. The reaction mixture was stirred at room temperature for 24 hours and then cooled to 5° C. The reaction mixture was combined with 100 ml of ethyl acetate and then with 100 ml of 20% hydrochloric acid. The mixture was stirred at room temperature for 3 hours and then extracted with toluene. Through conventional work-up including washing, drying and concentration, 8.0 g (yield 84%) of the target compound was obtained.

Workup

  1. customobtained in <7-1>
  2. temperatureThe solution was heated
  3. temperatureunder reflux
  4. customwas removed

Sources & evidence

ORD record
ord-f1b6a4381ae44f80881f77e2cda744b5
Source dataset
uspto-grants-2007_04
Patent number
US07202318B2

Reaction notes

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