Pyridine → 4-Dodecyloxycarbonylphthalic anhydride

HRID 890841Notes

Reaction equation

HRID 890841 reaction equation
[C:1](Cl)(=[O:14])[C:2]1[C:3](=[CH:7][C:8](=[CH:12][CH:13]=1)[C:9](Cl)=[O:10])[C:4](Cl)=[O:5].[O:16]1CCOCC1.[CH2:22]([OH:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].N1C=CC=CC=1>O>[CH2:22]([O:34][C:9]([C:8]1[CH:7]=[C:3]2[C:4](=[O:16])[O:5][C:1](=[O:14])[C:2]2=[CH:13][CH:12]=1)=[O:10])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 1049PyridineHCID 81931-DodecanolHCID 312751,4-Dioxane2×HCID 774721,2,4-Benzenetricarbonyl trichloride

Product 1

HCID 6063854-Dodecyloxycarbonylphthalic anhydrideYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 3-L flask equipped with a stirrer, a thermometer and a dropping funnel, 110 g (522.39 mmol) of anhydrous trimellitic chloride (4-chlorocarbonylphthalic anhydride) and 770 g of 1,4-dioxane were placed and were stirred at room temperature in an atmosphere of a nitrogen gas. To the resulting mixture, a mixture of 92.70 g (497.52 mmol) of 1-dodecanol, 41.32 g (522.39 mmol) of pyridine and 370 g of 1,4-dioxane was added dropwise over 1 hour. The mixture was stirred at room temperature for further 5 hours, followed by dropwise addition of 570 g of pure water over 30 minutes. Pyridine hydrochloride separated in a reaction system was then dissolved, and a crystal of target 4-dodecyloxycarbonylphthalic anhydride separated out. The resulting mixture was stirred for further 1 hour, the precipitate was separated by filtration and was rinsed with pure water, was then dried at 50° C. under reduced pressure and thereby yielded 145.26 g (402.99 mmol) of 4-dodecyloxycarbonylphthalic anhydride as a white powder. The yield was 80.1% on the basis of 1-dodecanol and 77.1% on the basis of anhydrous trimellitic chloride.

Workup

  1. customIn a 3-L flask equipped with a stirrer
  2. additionwas added dropwise over 1 hour
  3. stirringThe mixture was stirred at room temperature for further 5 hours
  4. customPyridine hydrochloride separated in a reaction system
  5. dissolutionwas then dissolved
  6. customa crystal of target 4-dodecyloxycarbonylphthalic anhydride separated out
  7. stirringThe resulting mixture was stirred for further 1 hour
  8. customthe precipitate was separated by filtration
  9. washwas rinsed with pure water
  10. customwas then dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-5dced9f10bfc40b0bccc642342a6f485
Source dataset
uspto-grants-2006_02
Patent number
US06998491B2

Reaction notes

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