Reaction #1810790

ord-581c18f00d20498ebc21c1af0e00e8f8

Reaction equation

Cl
hydrochloric acid
COC(=O)C(O)(C(F)(F)F)C(F)(F)F
methyl 2-hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionate
B.[Na]
sodium boron hydride
O
water
OCC(O)(C(F)(F)F)C(F)(F)F
3,3,3-trifluoro-2-trifluoromethyl-1,2-propane diol
Yield 96.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGStirring
  2. 2
    Otherto quench
  3. 3
    Otherthe reaction
  4. 4
    OtherThe organic layer was separated
  5. 5
    Concentrationconcentrated
  6. 6
    workup.DISTILLATIONdistilled

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07485408B2uspto-grants-2009_02