m-Chloroperbenzoic acid → HCID 178458816, compound

HRID 1193864Notes

Reaction equation

HRID 1193864 reaction equation
[C:1]([C:5]1[C:6](=[O:18])[CH2:7][CH:8]([C:12]2[CH2:13][O:14][CH2:15][CH2:16][CH:17]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[C:1]([C:5]1[C:10](=[O:11])[CH2:9][CH:8]([C:12]23[O:27][CH:17]2[CH2:16][CH2:15][O:14][CH2:13]3)[CH2:7][C:6]=1[OH:18])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178458873HCID 178458873, compound

Product 1

HCID 178458816HCID 178458816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14.8 parts by weight of 2-propionyl-5-(5,6-dihydro-2H-pyran-3-yl)-3-hydroxy-2-cyclohexen-1-one are dissolved in 100 parts by volume of dichloromethane, and m-chloroperbenzoic acid is added at room temperature, and the reaction is monitored by means of thin layer chromatography. After the reaction has ended, the precipitated m-chlorobenzoic acid is filtered off, the filtrate is washed twice with semiconcentrated sodium bicarbonate solution and water and dried over sodium sulfate, and the solvent is distilled off under reduced pressure to leave 2-propionyl-5-(3,4-epoxy-tetrahydropyran-3-yl)-3-hydroxy-2-cyclohexen-1-one (compound No. 30).

Workup

  1. additionis added at room temperature
  2. filtrationthe precipitated m-chlorobenzoic acid is filtered off
  3. washthe filtrate is washed twice with semiconcentrated sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-efcaa1cd98214521bd1ce3ff71755825
Source dataset
uspto-grants-1989_03
Patent number
US04812160

Reaction notes

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