Toluene → HCID 21102169, compound

HRID 2355976Notes

Reaction equation

HRID 2355976 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[CH:10]=[C:11]([CH2:21][OH:22])[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:14]=1[N+:15]([O-:17])=[O:16]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:14]=1[N+:15]([O-:17])=[O:16])[CH:21]=[O:22]

Participants

5

Reactant 2

HCID 1140TolueneHCID 21102171HCID 21102171, compound

Product 1

HCID 21102169HCID 21102169, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

In a flame-dried flask, manganese (IV) oxide (36.0 g, 414 mmol) was azeotropically dried with toluene. Then, a solution of (3-methyl-4,5-dinitrophenyl)methanol (3.2 g, 15 mmol) in chloroform (100 mL) was transferred to the flask containing the manganese dioxide. The reaction mixture was heated at 50° C. with stirring for 3 h. Upon completion of the reaction, the reaction mixture was filtered through a pad of Celite® to remove manganese dioxide and the Celite was washed with chloroform several time. The filtrate was evaporated to give the title compound (1.4 g, 44% yield). 1H-NMR (CDCl3, 300 MHz) δ 10.09 (s, 1H), 8.51 (s, 1H), 8.16 (s, 1H), 2.51 (s, 3H).

Workup

  1. customUpon completion of the reaction
  2. filtrationthe reaction mixture was filtered through a pad of Celite®
  3. customto remove manganese dioxide
  4. washthe Celite was washed with chloroform several time
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-ed6c52bc4ff044b3b8eb93f0dd7c2e0c
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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