Water → 4-Phenyl-2-trifluoromethyl-1,2-pentanediol

HRID 1066930Notes

Reaction equation

HRID 1066930 reaction equation
C([O:3][C:4](=O)[C:5]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[C:9]1([CH:7]([CH3:8])[CH2:6][C:5]([C:15]([F:16])([F:17])[F:18])([OH:19])[CH2:4][OH:3])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 179356082-Hydroxy-4-phenyl-2-trifluoromethyl-valeric acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 185512124-Phenyl-2-trifluoromethyl-1,2-pentanediolYield 110.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.35 g of 2-hydroxy-4-phenyl-2-trifluoromethyl-valeric acid ethyl ester is dissolved in 100 ml of diethyl ether and stirred at 0° C. with 1.3 g of lithium aluminum hydride for one hour at 0° C. and for 16 hours at room temperature. A little water is added while being cooled, and it is stirred for one hour. The diethyl ether phase is separated, dried (Na2SO4) and concentrated by evaporation and distilled on a bulb tube. 4.1 g of 4-phenyl-2-trifluoromethyl-1,2-pentanediol, boiling point 120° C./0.04 hPa, is obtained.

Workup

  1. temperaturewhile being cooled
  2. customThe diethyl ether phase is separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation
  5. distillationdistilled on a bulb tube

Sources & evidence

ORD record
ord-8e2cba78c4b3426cad1640213a2232ab
Source dataset
uspto-grants-2001_06
Patent number
US06245804B1

Reaction notes

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