HCID 67000256, compound → 4-Hydroxy-6-(trifluoromethyl)-2H-pyran-2-one

HRID 2237900Notes

Reaction equation

HRID 2237900 reaction equation
CC1(C)O[C:6](=[O:8])[CH:5]=[C:4]([CH2:9][C:10]([OH:16])(O)[C:11]([F:14])([F:13])[F:12])[O:3]1>C1(C)C=CC=CC=1>[OH:3][C:4]1[CH:9]=[C:10]([C:11]([F:12])([F:13])[F:14])[O:16][C:6](=[O:8])[CH:5]=1

Participants

3

Reactant 1

HCID 67000256HCID 67000256, compound

Product 1

HCID 670000654-Hydroxy-6-(trifluoromethyl)-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
23 °C

Procedure

A suspension of 2,2-dimethyl-6-(3,3,3-trifluoro-2,2-dihydroxy-propyl)-[1,3]dioxin-4-one (example C.22 step 1) (70 g, 273 mmol) in toluene (500 mL) was placed in a preheated (135° C.) oil bath, needed 10 min to reflux, then was refluxed for 25 min while distilling off about 150 mL of solvent. The hot solution was concentrated in vacuum to about 300 mL, some heptane was added, cooled to 23° C., filtered the precipitate off, washed with little cold toluene and dried in HV to give the title compound a light yellow solid (17.93 g, 36%). MS (ISN) 179.1 [(M−H)−].

Workup

  1. customwas placed in a preheated (135° C.) oil bath
  2. temperatureto reflux
  3. temperaturewas refluxed for 25 min
  4. distillationwhile distilling off about 150 mL of solvent
  5. concentrationThe hot solution was concentrated in vacuum to about 300 mL
  6. additionsome heptane was added
  7. filtrationfiltered the precipitate off,
  8. washwashed with little cold toluene
  9. customdried in HV

Sources & evidence

ORD record
ord-fd9e8f8d02ea44e3b800f01c779ed683
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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