Nitric Acid → Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate

HRID 596603Notes

Reaction equation

HRID 596603 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][CH2:12][O:13][C:6]=2[CH:5]=1.[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([N+:15]([O-:17])=[O:16])=[CH:8][C:7]2[O:10][CH2:11][CH2:12][O:13][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 3802178Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate

Product 1

HCID 10537941Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5.0 g. of 3,4-ethylenedioxybenzoic acid methyl ester in 5.0 mls. of glacial acetic acid is added dropwise 5.0 mls. of 70% nitric acid at 50°-60° C. After addition the reaction mixture is kept at 55° C. for one hour, then cooled and 50 mls. of ice water added. The resulting precipitate is recovered by filtering, water washed and dried to obtain 6-nitro-3,4-ethylenedioxybenzoic acid methyl ester, m.p. 115°-118° C.

Workup

  1. customat 50°-60° C
  2. additionAfter addition the reaction mixture
  3. temperaturecooled
  4. customThe resulting precipitate is recovered
  5. filtrationby filtering
  6. washwater washed
  7. customdried

Sources & evidence

ORD record
ord-5a4af898b3bc4654963153c4509d354d
Source dataset
uspto-grants-1977_03
Patent number
US04011323

Reaction notes

Loading…