m-Chloroperbenzoic acid → HCID 21831345, compound

HRID 1601405Notes

Reaction equation

HRID 1601405 reaction equation
[F:1][CH2:2][C:3]1([CH2:23][F:24])[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:12][C:5]=2[O:4]1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[O:33]1[CH:7]2[CH:8]1[C:3]([CH2:2][F:1])([CH2:23][F:24])[O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]([F:22])([F:21])[C:14]([F:19])([F:20])[C:15]([F:16])([F:17])[F:18])=[CH:9][C:6]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21831331HCID 21831331, compound

Product 1

HCID 21831345HCID 21831345, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.1 g of 2,2-bisfluoromethyl-6-heptafluoropropyl-2H-1-benzopyran, 4.20 g of m-chloroperbenzoic acid (70%) and 50 ml of methylene chloride was stirred at room temperature for 27 hours. After removal of the separated crystal by filtration, the filtrate was washed with saturated sodium hydrogen carbonate solution and saturated saline solution, and dried with sodium sulfate. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, hexane:CH2Cl2 =5:1) to obtain 1.44 g of oily 3,4-epoxy-2,2-bisfluoromethyl-6-heptafluoropropyl-3,4-dihydro-2H-1-benzopyran represented by the following formula.

Workup

  1. customAfter removal of the separated crystal
  2. filtrationby filtration
  3. washthe filtrate was washed with saturated sodium hydrogen carbonate solution and saturated saline solution
  4. dry with materialdried with sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe resultant residue was purified

Sources & evidence

ORD record
ord-94d077d82e784e61853ffafae5a09e82
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

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