Nitric Acid → 6-Nitro-5,8-dimethyl-1,4-benzodioxane

HRID 1376550Notes

Reaction equation

HRID 1376550 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[C:15]2CO[CH2:12][O:11][C:10]=2[C:9]([CH3:16])=[CH:8][CH:7]=1.C[C:18](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:19]>C(OC(=O)C)(=O)C>[N+:1]([C:7]1[CH:8]=[C:9]([CH3:16])[C:10]2[O:11][CH2:12][CH2:18][O:19][C:15]=2[C:6]=1[CH3:5])([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 218404815,8-Dimethyl-1,3-benzodioxane

Product 1

HCID 218404806-Nitro-5,8-dimethyl-1,4-benzodioxane

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 1.12 mL of concentrated nitric acid in 20 mL of acetic arthydride is added dropwise to a stirred solution of 2.90 g of 5,8-dimethyl-1,3-benzodioxane in 70 mL of acetic anhydride at -5° C. After 15 minutes, the mixture is poured over 100 g of crushed ice and allowed to stir for 30 minutes as a white precipitate falls out of solution. The solid is filtered and taken up in ether, dried over magnesium sulfate and concentrated under reduced pressure to afford 3.1 g of 6-nitro-5,8-dimethyl-1,4-benzodioxane.

Workup

  1. filtrationThe solid is filtered
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b50a33aa64fa4a4fb5c9e42639d59a5f
Source dataset
uspto-grants-1997_09
Patent number
US05663189

Reaction notes

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