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

HRID 1723608Notes

Reaction equation

HRID 1723608 reaction equation
[OH:1][C:2]([C:11]([F:14])([F:13])[F:12])([C:7]([F:10])([F:9])[F:8])[C:3](OC)=[O:4].B.[Na].O.Cl>C(OCC)C>[F:8][C:7]([F:9])([F:10])[C:2]([C:11]([F:12])([F:14])[F:13])([OH:1])[CH2:3][OH:4]

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

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

Workup

  1. stirringStirring
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-581c18f00d20498ebc21c1af0e00e8f8
Source dataset
uspto-grants-2009_02
Patent number
US07485408B2

Reaction notes

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