Acetic Acid → 4,5,6-Triethoxy-7-nitrophthalide

HRID 1788794Notes

Reaction equation

HRID 1788794 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8]1[C:17]([O:18][CH2:19][CH3:20])=[C:16]([O:21][CH2:22][CH3:23])[CH:15]=[C:14]2[C:9]=1[CH2:10][O:11][C:12]2=[O:13])[CH3:6].[N+:24]([O-])([OH:26])=[O:25]>O>[CH2:5]([O:7][C:8]1[C:17]([O:18][CH2:19][CH3:20])=[C:16]([O:21][CH2:22][CH3:23])[C:15]([N+:24]([O-:26])=[O:25])=[C:14]2[C:9]=1[CH2:10][O:11][C:12]2=[O:13])[CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 133178834,5,6-Triethoxyphthalide

Product 1

HCID 64521774,5,6-Triethoxy-7-nitrophthalideYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Glacial acetic acid (14 ml) was added to 5.32 g (0.02 mole) of 4,5,6-triethoxyphthalide. Into the reaction mixture on a water bath at 30-35° C., 14 ml of fuming nitric acid, d=1.52, was gradually added dropwise over a time period of 9 hours. After completion of the addition, the reaction mixture was allowed to stand overnight at room temperature and thereafter 80 ml of water was added to deposit crystals. The crystals were filtered out, washed thoroughly with water and dried. There was obtained 2.20 g of 4,5,6-triethoxy-7-nitrophthalide having a melting point of 82.5-84.5° C. with a yield of 35%.

Workup

  1. additionAfter completion of the addition
  2. filtrationThe crystals were filtered out
  3. washwashed thoroughly with water
  4. customdried

Sources & evidence

ORD record
ord-2a9efe2e38d441bdb33e0120ea48ea1f
Source dataset
uspto-grants-1987_08
Patent number
US04684732

Reaction notes

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