Toluene → HCID 86756384, compound

HRID 635158Notes

Reaction equation

HRID 635158 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[F:21][C:22]([C:28]([F:52])([F:51])[C:29]([F:50])([F:49])[C:30]([F:48])([F:47])[C:31]([F:46])([F:45])[C:32]([F:44])([F:43])[C:33]([F:42])([F:41])[C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])(O)[C:23]([F:26])([F:25])[F:24].C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:1]([O:20][C:22]([F:21])([C:28]([F:51])([F:52])[C:29]([F:49])([F:50])[C:30]([F:47])([F:48])[C:31]([F:45])([F:46])[C:32]([F:43])([F:44])[C:33]([F:42])([F:41])[C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])[C:23]([F:26])([F:25])[F:24])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 445639Oleic AcidHCID 86756383HCID 86756383, compound

Product 1

HCID 86756384HCID 86756384, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With 57 g of oleic acid were mixed 93 g of perfluorooctylethanol and 340 ml of toluene, and 3 g of p-toluenesulfonic acid was slowly added with stirring. The resulting mixture was vigorously refluxed for about 1 hour and 30 minutes to carry out the reaction until water was removed azeotropically. After completion of the reaction, the reaction mixture was cooled and then concentrated under reduced pressure to remove the toluene, and the residue was dissolved in 300 ml of n-hexane. The resulting solution was purified by a column chromatography to obtain 129 g (yield: 88%) of perfluorooctylethyl oleate.

Workup

  1. additionwas slowly added
  2. temperatureThe resulting mixture was vigorously refluxed for about 1 hour and 30 minutes
  3. customwas removed azeotropically
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture was cooled
  6. concentrationconcentrated under reduced pressure
  7. customto remove the toluene
  8. dissolutionthe residue was dissolved in 300 ml of n-hexane
  9. customThe resulting solution was purified by a column chromatography

Sources & evidence

ORD record
ord-4f5f454d4e0140b2823e5e9a56021bce
Source dataset
uspto-grants-2001_02
Patent number
US06187724B1

Reaction notes

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