m-Chloroperbenzoic acid → HCID 19610326, compound

HRID 1602092Notes

Reaction equation

HRID 1602092 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7](/[CH:16]=[C:17]2/[C:18](=[O:24])[N:19]([CH3:23])[CH2:20][CH2:21][S:22]/2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:30]>ClCCl>[CH3:4][C:2]([C:5]1[CH:6]=[C:7](/[CH:16]=[C:17]2/[C:18](=[O:24])[N:19]([CH3:23])[CH2:20][CH2:21][S:22]/2=[O:30])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19610362HCID 19610362, compound

Product 1

HCID 19610326HCID 19610326, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (Z)-2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-methyl-3-thiomorpholinone (1.25 g, 3.6 mmol) in dichloromethane (18 ml) was cooled under nitrogen to 0° C. A solution of m-chioroperoxybenzoic acid (0.78 g, 3.6 mmol) in dichloromethane (llml) was then added dropwise over 5 minutes. The reaction mixture was stirred an additional 25 minutes and washed once with saturated sodium bicarbonate. The organic layer was dried over sodium sulfate. Rotary evaporation gave crude product which was crystallized from ethyl acetate-hexane to give desired product (1.04 g, 79%):

Workup

  1. washwashed once with saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customRotary evaporation
  4. customgave crude product which
  5. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-209206fa0b4b4934972057c5f578ffca
Source dataset
uspto-grants-1999_11
Patent number
US05981523

Reaction notes

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