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

HRID 1293708Notes

Reaction equation

HRID 1293708 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.) oilbath, 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.) oilbath
  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-1a8a9e43275d42b9a7bf0f0e6a6f9baf
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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