Nitromethane → HCID 70622774, compound

HRID 1834853Notes

Reaction equation

HRID 1834853 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([CH:14]=O)[CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2.C([O-])(=O)C.[NH4+].[N+:21]([CH3:24])([O-:23])=[O:22]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([CH:14]=[CH:24][N+:21]([O-:23])=[O:22])[CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 20372185HCID 20372185, compound

Product 1

HCID 70622774HCID 70622774, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 2 liter 3-necked flask fitted with a condenser and thermometer and magnetically stirred, 126.7 g (0.613 mole) of 4,5-dimethoxy-6-indanaldehyde, 29.3 g (0.380 mole) of ammonium acetate, 127 ml (2.82 mole) of nitromethane and 390 ml of acetic acid were heated at 112° C for 45 minutes. After cooling in the refrigerator and scratching with a glass rod the solution crystallized. After filtering and washing with cold acetic acid the product was dried under vacuum overnight and recrystallized from methanol yielding 104.4 g (68%) of 4,5-dimethoxy-6-nitrovinylindane as yellow needles, m.p. 103.5°-104.5° C. Anal. Calcd. for C13H15NO4 : C, 62.64; H, 6.06; N, 5.62. Found: C, 62.45; H, 6.17; N, 5.84.

Workup

  1. customIn a 2 liter 3-necked flask fitted with a condenser
  2. temperatureAfter cooling in the refrigerator
  3. customcrystallized
  4. filtrationAfter filtering
  5. washwashing with cold acetic acid the product
  6. customwas dried under vacuum overnight
  7. customrecrystallized from methanol yielding 104.4 g (68%) of 4,5-dimethoxy-6-nitrovinylindane as yellow needles, m.p. 103.5°-104.5° C

Sources & evidence

ORD record
ord-e9490f3ce8cf4ebaa1993c8b256a9311
Source dataset
uspto-grants-1978_01
Patent number
US04071562

Reaction notes

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