m-Chloroperbenzoic acid → 3-(3,4-Dichlorophenyl)-1,4-oxathiane 4-oxide

HRID 274343Notes

Reaction equation

HRID 274343 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[S:14][CH2:13][CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=C(C=CC=1)C(OO)=[O:20].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[S:14](=[O:20])[CH2:13][CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 200931953-(3,4-Dichlorophenyl)-1,4-oxathiane

Product 1

HCID 200931943-(3,4-Dichlorophenyl)-1,4-oxathiane 4-oxideYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 3-(3,4-dichlorophenyl)-1,4-oxathiane (1 g, 4 mmol) in dichloromethane (10 ml) at 0° C. was treated with a solution of meta-chloroperoxybenzoic acid (85%, 860 mg, 4 mmol) in dichloromethane (10 ml) and stirred at 0° C. for 30 mins then at room temperature for 3 hrs. The mixture was shaken with aqueous sodium bicarbonate solution and the organic phase separated, dried (MgSO4) and evaporated to give a solid which was triturated with hexane/toluene (1:1) to give 3-(3,4-dichlorophenyl)-1,4-oxathiane 4-oxide (860 mg), as a colourless crystalline solid, m.p. 100°-103° C.;

Workup

  1. waitat room temperature for 3 hrs
  2. customthe organic phase separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a solid which
  6. customwas triturated with hexane/toluene (1:1)

Sources & evidence

ORD record
ord-38e2063268b84022afa969a25c867dc9
Source dataset
uspto-grants-1995_02
Patent number
US05389649

Reaction notes

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