m-Chloroperbenzoic acid → HCID 86718021, compound

HRID 1500484Notes

Reaction equation

HRID 1500484 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[OH:14])[CH:2]=[CH2:3].C1C=C(Cl)C=C(C(OO)=[O:23])C=1.OS([O-])=O.[Na+]>C(Cl)(Cl)Cl>[CH3:10][C:8]1[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]2[O:14][CH:2]([CH2:3][OH:23])[CH2:1][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86718022HCID 86718022, compound

Product 1

HCID 86718021HCID 86718021, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-allyl-4-methyl-6-nitrophenol (7b) (0.50 g, 2.5 mmol) and m-CPBA (0.64 g, 2.5 mmol) in CHCl3 (9 mL) was stirred for 6 h at 85° C. The mixture was poured into saturated NaHSO3 (20 mL), extracted with DCM (40 mL), washed with brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1) to give the title compound (7c) as a solid. MS-ESI (m/z): 210 (M+1)+.

Workup

  1. extractionextracted with DCM (40 mL)
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1)

Sources & evidence

ORD record
ord-6fa1543252dd4fa08e1bfad632358694
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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