m-Chloroperbenzoic acid → HCID 13938213, compound

HRID 2308886Notes

Reaction equation

HRID 2308886 reaction equation
[Si:1]([O:8][C:9]1[C:10]([CH3:20])=[C:11]([CH3:19])[C:12]2[O:16][CH2:15][S:14][C:13]=2[C:17]=1[CH3:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:29])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Si:1]([O:8][C:9]1[C:10]([CH3:20])=[C:11]([CH3:19])[C:12]2[O:16][CH2:15][S:14](=[O:29])[C:13]=2[C:17]=1[CH3:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14802197HCID 14802197, compound

Product 1

HCID 13938213HCID 13938213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The whole of the 5-t-butyldimethylsilyloxy-4,6,7-trimethyl-1,3-benzoxathiole obtained as described in Example 92 was dissolved in 100 ml of methylene chloride, and 0.99 g of m-chloroperbenzoic acid was added, with ice cooling, to the resulting solution. The reaction mixture was then stirred for 1 hour at the same temperature, after which it was poured into a saturated aqueous solution of sodium bicarbonate, extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off, whereupon the residue crystallized. The crystals were washed with carbon tetrachloride, yielding 1.30 g of the title compound, melting at 100°-101° C.

Workup

  1. extractionextracted with chloroform
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off, whereupon the residue
  5. customcrystallized
  6. washThe crystals were washed with carbon tetrachloride

Sources & evidence

ORD record
ord-d6db361b14d24aa1bd2e62ba54dbb82e
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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