Acetate → Cyanuric acid

HRID 1700050Notes

Reaction equation

HRID 1700050 reaction equation
C([O-])(=O)C.Cl[N:6]1[C:11](=[O:12])[N:10](Cl)[C:9](=[O:14])[N:8](Cl)[C:7]1=[O:16]>CCCCCC>[NH:6]1[C:11](=[O:12])[NH:10][C:9](=[O:14])[NH:8][C:7]1=[O:16]

Participants

4

Reactant 2

HCID 175AcetateHCID 6909Trichloroisocyanuric Acid2×

Product 1

HCID 7956Cyanuric acid

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

40 g (20.4 mmol) of geranil acetate was dissolved in 100 ml of n-hexane. After adding 17.1 g (70.0 mmol) of trichloroisocyanuric acid slowly, the mixture was maintained at −10° C. to 0° C. for six hours. After the completion of the reaction, remaining trichloroisocyanuric acid and by-produced isocyanuric acid were removed out of the system by filtration. The filtrate was washed with a 5% aqueous solution of sodium hydrogencarbonate and ion-exchange water in order, and dried over anhydrous sodium sulfate. After removal of the solvent, a crude product was obtained. The crude product was subjected to silica gel column chromatography to give desired 6-chloro-3,7-dimethyl-2,7-octatrienyl acetate as pale yellow oil in a yield of 86%.

Workup

  1. temperaturethe mixture was maintained at −10° C. to 0° C. for six hours
  2. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-73f050133df8454f991f990add9fdcf2
Source dataset
uspto-grants-2002_02
Patent number
US06348622B1

Reaction notes

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