2,5-Dihydroxybenzoic acid → HCID 20600087, compound

HRID 2308120Notes

Reaction equation

HRID 2308120 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:38])[C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1>CN(C)C=O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:38])[C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1)=[O:5]

Participants

4

Reactant 2

HCID 34692,5-Dihydroxybenzoic acidHCID 22177449HCID 22177449, compound

Product 1

HCID 20600087HCID 20600087, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2.78 g (18.0 mmol) 2,5-dihydroxybenzoic acid was dissolved in 36 ml dimethylformamide. 2.96 ml (19.8 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene(1,5-5) (DBU) was added dropwise in the course of 15 minutes. The reaction temperature rose to 30° C. and 8.83 g (19.8 mmol) 3,5-dinitrobenzoic acid 11-bromoundecyl ester was subsequently added in one portion. The mixture was then heated at 80° C. for 2 hours. The reaction mixture was cooled and then partitioned between dichloromethane and 1N hydrochloric acid; the organic phase was washed twice with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using Toluene yielded 5.28 g (57%) 3,5-dinitrobenzoic acid 11-[2,5-dihydroxybenzoyloxy]undecyl ester as yellow powder.

Workup

  1. customrose to 30° C.
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between dichloromethane and 1N hydrochloric acid
  4. washthe organic phase was washed twice with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-81b3b310d19e49da8bc5c5d30bbb4794
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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