Sodium Bicarbonate → HCID 86663810, compound

HRID 2367719Notes

Reaction equation

HRID 2367719 reaction equation
O.[C:2]1(C)C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]([F:22])([C:18]([OH:21])([CH3:20])[CH3:19])[C:15]([OH:17])=[O:16].C(=O)([O-])O.[Na+]>CO>[F:13][C:14]([F:22])([C:18]([OH:21])([CH3:20])[CH3:19])[C:15]([O:17][CH3:2])=[O:16]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 107731732,2-difluoro-3-hydroxy-3-methyl-butanoic acid

Product 1

HCID 86663810HCID 86663810, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A catalytic amount of p-toluenesulfonic acid monohydrate was added to a mixture of 73.3 g of Intermediate 3 in Example 3 and 300 g of methanol. With stirring in a nitrogen atmosphere, the reaction mixture was heated under reflux for 12 hours. After cooling, the reaction mixture was poured into a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The ethyl acetate solution was washed, dried and concentrated. The residue was distilled in vacuum, obtaining 52.0 g (yield 65%) of methyl 2,2-difluoro-3-hydroxy-3-methylbutanoate.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution was washed
  6. customdried
  7. concentrationconcentrated
  8. distillationThe residue was distilled in vacuum

Sources & evidence

ORD record
ord-066b4d2080cd4a59a3a9607da73fa648
Source dataset
uspto-grants-2014_04
Patent number
US08697903B2

Reaction notes

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