m-Chloroperbenzoic acid → HCID 18330057, compound

HRID 2271040Notes

Reaction equation

HRID 2271040 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=C(Cl)C=C(C(OO)=[O:22])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:22]1[C:10]2[CH2:9][CH2:8][C:7]3[C:12]([C:11]1=2)=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14566727HCID 14566727, compound

Product 1

HCID 18330057HCID 18330057, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-nitro-3,4-dihydronaphthalene (9.18 g; 0.052 mol) (from Preparation 2) in CH2Cl2 (600 ml) was cooled to 0° C. and treated with m-CPBA, 57-85%, (13.86 g, approx. 0.056 mol, approx. 1.1 equiv). The reaction mixture was allowed to stir for 48 h, slowly warming to room temperature. The mixture was treated with aqueous NaHCO3 (300 ml) and the organic layer was separated. The organic layer was extracted with additional aqueous NaHCO3, washed with aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure to give 1,2-epoxy-7-nitro-3,4-dihydronaphthalene (9.94, 100%) as a white solid which was used in the next step without further purification. Rf (silica gel): 0.56(70% hexane: 30% EtOAc); 1H NMR (300 MHZ, CDCl3) 8.24 (s, 1H), 8.08 (dd, J=1.8 and 8.1 H 1H), 7.23 (d, J=8.1 Hz, 1H), 3.92 (d, J=4.2 Hz, 1H), 3.77 (s, 1H), 2.87-2.62 (m, 2H), 2.47 (dd, J=6.6 and 14.4 Hz, 1H), 1.78 (dt, J=5.7 and 14.1 Hz, 1H), 13C NMR (75 MHZ, CDCl3) 146.5, 144.7, 134.5, 129.4, 124.4, 123.4, 54.7, 51.8, 24.5, 21.0.

Workup

  1. customthe organic layer was separated
  2. extractionThe organic layer was extracted with additional aqueous NaHCO3
  3. washwashed with aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92c4c509bb4a4f17a0dd12253a0dfc66
Source dataset
uspto-grants-2001_12
Patent number
US06333337B1

Reaction notes

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