3,5-Dinitrobenzoic acid → HCID 22177420, compound

HRID 1797340Notes

Reaction equation

HRID 1797340 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[OH:16][C:17]1[CH:18]=[C:19]([CH:30]=[C:31]([OH:33])[CH:32]=1)[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Cl)=[O:21]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:16][C:17]1[CH:18]=[C:19]([CH:30]=[C:31]([OH:33])[CH:32]=1)[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:8][C:7](=[O:9])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1)=[O:21]

Participants

5

Reactant 2

HCID 74333,5-Dinitrobenzoic acidHCID 22177393HCID 22177393, compound

Product 1

HCID 22177420HCID 22177420, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
84 °C

Procedure

1.960 g (9.2 mmol) 3,5-dinitrobenzoic acid was suspended in 10 ml N,N-dimethylformamide. 1.407 g (9.2 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene(1,5-5) (DBU) were added dropwise over a period of 10 minutes, and 0.708 g (1.9 mmol) tetrabutylammonium iodide were added. A solution of 2.3 g (8.2 mmol) 6-chlorohexyl 3,5-dihydroxybenzoate and 15 ml N,N-dimethylformamide were added and the resulting mixture was then heated to 84° C. for 22 hours. The reaction mixture was cooled and then partitioned between ethyl acetate and water. The organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 110 g silica gel using first cyclohexane:ethyl acetate (7:3) then (3:2) as eluant yielded 2.3 g (56%) of 6-[(3,5-dinitrobenzoyl)oxy]hexyl 3,5-dihydroxybenzoate as yellow crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-c30d0ec2b94b4b04824a404576419bf6
Source dataset
uspto-grants-2006_04
Patent number
US07034098B2

Reaction notes

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