Methanol → HCID 15662884, compound

HRID 487728Notes

Reaction equation

HRID 487728 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[C:5]=1C=O)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:26])C=1.[OH-].[K+].CO>C(Cl)(Cl)Cl>[OH:26][C:5]1[C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[C:10]([O:12][CH3:13])=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 123200312,3,4-Trimethoxy-6-nitrobenzaldehyde

Product 1

HCID 15662884HCID 15662884, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-nitro-4,5,6-trimethoxybenzaldehyde (19.3 g, 0.08 mol) and m-chloroperbenzoic acid (20.7 g, 0.12 mol) in chloroform (350 ml) was heated under reflux for 5 hours. After cooling, the reaction mixture was washed with 10% sodium bicarbonate solution and water. The solvent was removed by evaporation in vacuo and the residue was then treated with a mixture of 10% potassium hydroxide solution (potassium hydroxide 5.0 g, 0.088 mol in 50 ml of water) and methanol (150 ml) at room temperature under nitrogen. The solvent was removed in vacuo and the solid residue was dissolved in water (300 ml) and then acidified with 6N hydrochloric acid. The precipitated product was collected by filtration, washed well with water and dried to give (after recrystallization from 2-propanol) 13.1 g of 2-hydroxy-1-nitro-3,4,5-trimethoxybenzene, mp 72-73° C. 1H-NMR (CDCl3): δ3.87, 3.94, and 4.08 (each 3H, s, 3 ×OMe), 7.32 (1H, s, H-6), 10.78 (1H, exchangeable, OH). Analyses: Calculated for C9H11NO6 : C, 47.16; H, 4.84; N, 6.11. Found: C, 47.11; H, 5.00; N, 6.17.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with 10% sodium bicarbonate solution and water
  5. customThe solvent was removed by evaporation in vacuo
  6. customThe solvent was removed in vacuo
  7. dissolutionthe solid residue was dissolved in water (300 ml)
  8. filtrationThe precipitated product was collected by filtration
  9. washwashed well with water
  10. customdried

Sources & evidence

ORD record
ord-55540ad01e8548f9a23aba7cd50e9fa9
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

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