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

HRID 2360749

Reaction equation

HRID 2360749 reaction equation
B.[Na].C(OC(C)C)(C)C.[OH-].[Na+].[F:12][C:13]([F:25])([F:24])[C:14]([OH:23])([C:19]([F:22])([F:21])[F:20])[C:15](OC)=[O:16].Cl>O>[F:12][C:13]([F:24])([F:25])[C:14]([C:19]([F:20])([F:22])[F:21])([OH:23])[CH2:15][OH:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 14798Sodium HydroxideHCID 9877912Methyl 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropionateHCID 178418435HCID 178418435, compound

Product 1

HCID 118056773,3,3-Trifluoro-2-(trifluoromethyl)-1,2-propanediolYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Synthesis was carried out in accordance with the procedure described in U.S. Pat. No. 7,868,199. In a nitrogen atmosphere, 84 g of sodium boron hydride, 1,450 g of diisopropyl ether (IPE), 2,000 g of water and 1.7 g of 25 wt % NaOH aqueous solution were ice cooled, to which 500 g of methyl 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propanoate was added dropwise. Stirring was continued for 24 hours at room temperature. Under ice cooling, 444 g of 20 wt % hydrochloric acid aqueous solution was added dropwise to quench the reaction. After the water layer was removed, the organic layer was washed with water and concentrated at 50° C. and a slightly reduced pressure of 6.7 kPa, obtaining 682 g of a 61 wt % IPE solution of 3,3,3-trifluoro-2-trifluoromethyl-1,2-propane diol (yield 95%). The compound was used in the subsequent reaction without further purification.

Workup

  1. customSynthesis
  2. additionwas added dropwise
  3. customto quench
  4. customthe reaction
  5. customAfter the water layer was removed
  6. washthe organic layer was washed with water
  7. concentrationconcentrated at 50° C.

Sources & evidence

ORD record
ord-c568f7b39c914a7eac856c75a3a56c3b
Source dataset
uspto-grants-2014_04
Patent number
US08686166B2

Linked notes

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