m-Chloroperbenzoic acid → HCID 66779928, compound

HRID 1753267Notes

Reaction equation

HRID 1753267 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.ClC1C=C(C=CC=1)C(OO)=[O:24]>ClCCl>[O:24]=[C:2]1[O:1][CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66780421HCID 66780421, compound

Product 1

HCID 66779928HCID 66779928, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Product from step 2 (10.0 g, 38.5 mmol) was dissolved in 50 mL of dichloromethane and added dropwise into a solution of 3-chloroperoxybenzoic acid (99.3 g, 42.4 mmol) in dichloromethane (50 mL). The mixture was stirred for 24 h and then filtered. The solution obtained was washed twice with NaHCO3 (2 M) and once with brine. The extracted product was then purified by column chromatography (by silica gel using hexane/EtOAc gradient as eluent). The monomer was obtained as a white crystalline powder. Yield: 70%.

Workup

  1. filtrationfiltered
  2. customThe solution obtained
  3. washwas washed twice with NaHCO3 (2 M) and once with brine
  4. customThe extracted product was then purified by column chromatography (by silica gel using hexane/EtOAc gradient as eluent)
  5. customThe monomer was obtained as a white crystalline powder

Sources & evidence

ORD record
ord-663721091cf7468db676e55def81d418
Source dataset
uspto-grants-2015_10
Patent number
US09163114B2

Reaction notes

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