Hydrochloric Acid → 3,3,3-Trifluoro-2-(trifluoromethyl)-1,2-propanediol

HRID 252691

Reaction equation

HRID 252691 reaction equation
B.[Na].O.[OH:4][C:5]([C:14]([F:17])([F:16])[F:15])([C:10]([F:13])([F:12])[F:11])[C:6](OC)=[O:7].Cl>C(OCC)C>[F:11][C:10]([F:12])([F:13])[C:5]([C:14]([F:15])([F:17])[F:16])([OH:4])[CH2:6][OH:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9877912Methyl 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropionateHCID 178418435HCID 178418435, compound

Product 1

HCID 118056773,3,3-Trifluoro-2-(trifluoromethyl)-1,2-propanediolYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 25.0 g of sodium boron hydride, 500 g of water, and 500 g of diethyl ether, with stirring, 100 g of methyl 2-hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionate was added dropwise. The mixture was stirred for 10 hours, after which hydrochloric acid was added to quench the reaction. An organic layer was separated from the reaction mixture, concentrated, and distilled, obtaining 83.9 g of 3,3,3-trifluoro-2-trifluoromethyl-1,2-propane diol (yield 96%).

Workup

  1. stirringThe mixture was stirred for 10 hours
  2. customto quench
  3. customthe reaction
  4. customAn organic layer was separated from the reaction mixture
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-cbe3052df8844e5e83630c10c2df9151
Source dataset
uspto-grants-2011_01
Patent number
US07868199B2

Linked notes

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