1,4-Benzodioxan → 6,7-Dichloro-2,3-dihydro-1,4-benzodioxine

HRID 963333Notes

Reaction equation

HRID 963333 reaction equation
[Cl:1][C:2]1[C:3]([N+]([O-])=O)=[C:4]2[O:15][CH2:14][CH2:13][O:12][C:5]2=[C:6](C(=O)C)[C:7]=1[Cl:8].O1C2C=CC=CC=2OCC1>>[Cl:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]2[O:15][CH2:14][CH2:13][O:12][C:5]=2[CH:6]=1

Participants

3

Reactant 2

HCID 103011,4-BenzodioxanHCID 27636871-(6,7-dichloro-8-nitro-2,3-dihydro-1,4-benzodioxin-5-yl)-1-ethanone

Product 1

HCID 123986886,7-Dichloro-2,3-dihydro-1,4-benzodioxine

Procedure

The 5',6'-dichloro-2',3'-ethylenedioxy-4'-nitroacetophenone can be prepared by chlorinating 1,4-benzodioxane to give 6,7-dichloro-1,4-benzodioxane and then acetylating. The chlorination can be carried out by treating the benzodioxane with chlorine gas in acetic acid at 0 to 20° C. and requires 1 to 8 hours. The acetylation can be effected by reacting the 6,7-dichloro-1,4-benzodioxane with acetyl chloride in the presence of a Lewis acid in a suitable solvent (e.g., 1,2-dichloroethane, carbon disulfide, nitrobeanzene, etc.) at 20 to 40° C. and requires 24 to 48 hours.

Sources & evidence

ORD record
ord-a3ed5fe55d414e6690d99f1eb7dd0882
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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