m-Chloroperbenzoic acid → 2,6-Di-tert-butyl-4-[2-(methanesulfinyl)-1,3-thiazol-4-yl]phenol

HRID 980349Notes

Reaction equation

HRID 980349 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]([S:21][CH3:22])[S:19][CH:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[C:12]([C:9]1[CH:8]=[C:7]([C:16]2[N:17]=[C:18]([S:21]([CH3:22])=[O:31])[S:19][CH:20]=2)[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 135636842,6-Di-tert-butyl-4-[2-(methylsulfanyl)-1,3-thiazol-4-yl]phenol

Product 1

HCID 131070562,6-Di-tert-butyl-4-[2-(methanesulfinyl)-1,3-thiazol-4-yl]phenolYield 55.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 5 ml of chloroform was dissolved 0.8 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylthiothiazole and then 0.4 g of m-chloroperbenzoic acid (80%) was added portionwise to the solution with stirring. After 30 minutes since then, the reaction mixture was washed with an aqueous 5% sodium hydrogencarbonate solution and the chloroform layer was concentrated. The crystals thus obtained were recrystallized from hexane to provide 0.45 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylsulfinylthiazole.

Workup

  1. washAfter 30 minutes since then, the reaction mixture was washed with an aqueous 5% sodium hydrogencarbonate solution
  2. concentrationthe chloroform layer was concentrated
  3. customThe crystals thus obtained
  4. customwere recrystallized from hexane

Sources & evidence

ORD record
ord-f9851eec962d438686233e6f7b3077cb
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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