Nitric Acid → 1-(6,7-dichloro-8-nitro-2,3-dihydro-1,4-benzodioxin-5-yl)-1-ethanone

HRID 963360Notes

Reaction equation

HRID 963360 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[O:15][CH2:14][CH2:13][O:12][C:5]2=[C:6]([C:9](=[O:11])[CH3:10])[C:7]=1[Cl:8].[N+:16]([O-])([OH:18])=[O:17]>>[Cl:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]2[O:15][CH2:14][CH2:13][O:12][C:5]2=[C:6]([C:9](=[O:11])[CH3:10])[C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 27635631-(6,7-dichloro-2,3-dihydro-1,4-benzodioxin-5-yl)-1-ethanone

Product 1

HCID 27636871-(6,7-dichloro-8-nitro-2,3-dihydro-1,4-benzodioxin-5-yl)-1-ethanone

Procedure

5',6'-Dichloro-2',3'-ethylenedioxyacetophenone (8.5 g, 0.0344 miol) was added in portions to 34.5 mL of stirring fuming nitric acid at a rate such that the temperature of the reaction mixture remained below 10° C. The mixture was stirred for an additional 10 minutes at 5 C. and then poured onto 250 g of crushed ice giving yellow precipitate. The precipitate was isolated by filtration and washed with water. Drying gave 5',6'-dichloro-2',3'-ethylenedioxy-4'-nitroacetophenone (8.9 g, 0.0341 mol), m.p. 181°-182° C.

Workup

  1. customremained below 10° C
  2. customThe precipitate was isolated by filtration
  3. washwashed with water
  4. customDrying

Sources & evidence

ORD record
ord-199a65e8c5804e78ad618228faf36dbc
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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