m-Chloroperbenzoic acid → methyl 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenoxy]ethyl sulphoxide

HRID 2165529Notes

Reaction equation

HRID 2165529 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:27])=[CH:15]/[C:16]3[CH:26]=[CH:25][C:19]([O:20][CH2:21][CH2:22][S:23][CH3:24])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.ClC1C=CC=C(C(OO)=[O:37])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:27])=[CH:15]/[C:16]3[CH:26]=[CH:25][C:19]([O:20][CH2:21][CH2:22][S:23]([CH3:24])=[O:37])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67786645methyl 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]phenoxy]ethyl sulphide

Product 1

HCID 67785925methyl 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenoxy]ethyl sulphoxideYield 77.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.1 g of the compound obtained in Example 5 are dissolved in 50 ml of chloroform and treated slowly at 0° with a solution of 1.2 g of m-chloroperbenzoic acid (90%) in 10 ml of chloroform. After stirring at 0° for 20 hours the mixture is washed with dilute soda solution and water, dried and evaporated. The thus-obtained yellow oil is filtered over a small silica gel column (eluting agent hexane/ethyl acetate=1:2) and recrystallized from ethyl acetate. There are obtained 1.7 g of methyl 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenoxy]ethyl sulphoxide, melting point 134°-136°.

Workup

  1. washis washed
  2. additionwith dilute soda solution and water
  3. customdried
  4. customevaporated
  5. filtrationThe thus-obtained yellow oil is filtered over a small silica gel column (eluting agent hexane/ethyl acetate=1:2)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8e6e9c59f9f74d83a96a0ff050c2826d
Source dataset
uspto-grants-1990_07
Patent number
US04940707

Reaction notes

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