Toluene → HCID 59021286, compound

HRID 1445303Notes

Reaction equation

HRID 1445303 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([C:14]([F:17])([F:16])[F:15])([OH:13])[C:4]([F:12])([F:11])[CH:5]([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(CC)CC)C.C1(C)C=CC=CC=1.[C:34](Cl)(=[O:38])[C:35]([CH3:37])=[CH2:36]>O>[C:34]([O:10][CH:5]([C:6]([F:9])([F:8])[F:7])[C:4]([F:11])([F:12])[C:3]([OH:13])([C:14]([F:15])([F:16])[F:17])[C:2]([F:18])([F:19])[F:1])(=[O:38])[C:35]([CH3:37])=[CH2:36]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 59021298HCID 59021298, compound

Product 1

HCID 59021286HCID 59021286, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 138 g of 1,1,1,3,3,5,5,5-octafluoro-2-(trifluoromethyl)pentane-2,4-diol (Synthesis Example [1-1]), 53.0 g of triethylamine, and 700 g of toluene, under ice cooling and with stirring, 45.4 g of methacrylic acid chloride was added dropwise. The mixture was stirred for 2 hours. Water was added to the reaction mixture to quench the reaction, followed by conventional work-up steps of washing, drying and concentration to give a crude product. It was purified by silica gel column chromatography, yielding 119 g (yield 71%) of the end compound, fluorinated ester.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customto quench
  3. customthe reaction
  4. washof washing
  5. customdrying
  6. concentrationconcentration
  7. customto give a crude product
  8. customIt was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2cb5359cfba94259ab0c07454b1bc4d4
Source dataset
uspto-grants-2010_02
Patent number
US07666571B2

Reaction notes

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