m-Chloroperbenzoic acid → HCID 14820152, compound

HRID 2166393Notes

Reaction equation

HRID 2166393 reaction equation
[C:1]([C:4]1[C:16]([OH:17])=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])=[C:6]([CH2:18][CH:19]=[CH2:20])[CH:5]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[C:1]([C:4]1[C:16]([OH:17])=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])=[C:6]([CH2:18][CH:19]([OH:29])[CH3:20])[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14820095HCID 14820095, compound

Product 1

HCID 14820152HCID 14820152, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.46 g of 5-[4-acetyl-5-hydroxy-2-allylphenoxy]pentanenitrile in 100 ml of methylene chloride were added 6.1 g of 85% meta-chloroperbenzoic acid. After stirring for 5 hours, the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and a cold sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo to approximately 35 ml. The solution was placed in a freezer overnight providing 4.08 g of the crystalline title product which were recovered by filtration, m.p. 86°-87° C.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo to approximately 35 ml
  6. waitThe solution was placed in a freezer overnight

Sources & evidence

ORD record
ord-5475a9c47a6a43489d2643a3bb74ba4d
Source dataset
uspto-grants-1990_07
Patent number
US04945099

Reaction notes

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