m-Chloroperbenzoic acid → 2-(1-Chloro-3-methylnaphthalen-2-yl)oxirane

HRID 926219Notes

Reaction equation

HRID 926219 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[CH:13]=[CH2:14].ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[CH:13]1[CH2:14][O:20]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 671260761-Chloro-3-methyl-2-vinylnaphthalene

Product 1

HCID 896765372-(1-Chloro-3-methylnaphthalen-2-yl)oxirane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-chloro-3-methyl-2-vinyl-naphthalene (3.0 g, 14.8 mmol) in CH2Cl2 (120 mL) was added 3-chloroperoxybenzoic acid (3.8 g, 22.0 mmol) at 0° C. and allowed to warm to room temperature overnight. The reaction mixture was washed with NaHCO3, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give 2-(1-chloro-3-methylnaphthalen-2-yl)oxirane. 1H-NMR: 400 MHz, (CDCl3) δ 8.26 (d, J=7.2 Hz, 1H), 7.74 (dd, J=7.2, 2.0 Hz, 1H), 7.57-7.48 (m, 3H), 4.13 (t, J=3.6 Hz, 1H), 3.34 (t, J=5.6 Hz, 1H), 2.97 (dd, J=5.2, 2.8 Hz, 1H), 2.64 (s, 3H).

Workup

  1. washThe reaction mixture was washed with NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f0506780bca840c6a159c208ca746abd
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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