m-Chloroperbenzoic acid → HCID 67745330, compound

HRID 375486Notes

Reaction equation

HRID 375486 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]1([C:18]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22][S:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])O.[K+]>ClCCl>[C:12]1([C:18]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:20][S:21](=[O:6])[CH2:22][CH2:23]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516893Potassium BicarbonateHCID 57236704HCID 57236704, compound

Product 1

HCID 67745330HCID 67745330, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 20.3 g of 3-chloroperoxybenzoic acid (at 85%) in 300 cm3 of dichloromethane is added over 40 minutes to a solution, cooled to 0° C., of 25.4 g of 4,4-diphenyltetrahydrothiapyran in 130 cm3 of dichloromethane After stirring for 2 hours at 0° C., 250 cm3 of a 5% aqueous solution of potassium hydrogen carbonate are added to the mixture and it is then stirred for 15 minutes. The organic phase is again washed with 250 cm3 of a solution of potassium hydrogen carbonate and it is then dried over magnesium sulphate and concentrated to dryness (after verifying the absence of peroxides) under reduced pressure (2.7 kPa). 26.9 g of 4,4-diphenyltetrahydrothiapyran 1-oxide are obtained in the form of a white solid; melting point 122° C.

Workup

  1. stirringis then stirred for 15 minutes
  2. washThe organic phase is again washed with 250 cm3 of a solution of potassium hydrogen carbonate and it
  3. dry with materialis then dried over magnesium sulphate
  4. concentrationconcentrated to dryness (

Sources & evidence

ORD record
ord-fe804654e64b4eb09c0ce39b50629943
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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