Triethylamine → 2-Nitrobenzyl perfluorooctanoate

HRID 649703

Reaction equation

HRID 649703 reaction equation
[F:1][C:2]([F:25])([C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3](Cl)=[O:4].[N+:26]([C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][OH:32])([O-:28])=[O:27].C(N(CC)CC)C.Cl.C(N(CC)CC)C>C1C=CC=CC=1>[F:1][C:2]([F:25])([C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3]([O:32][CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=1[N+:26]([O-:28])=[O:27])=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 119232-Nitrobenzyl alcoholHCID 78978Perfluorooctanoyl chloride

Product 1

HCID 150954062-Nitrobenzyl perfluorooctanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Perfluorooctanoyl chloride (21.6 g, 0.05 mol) was added slowly with stirring to a solution of 2-nitrobenzyl alcohol (7.65 g, 0.05 mol) and triethylamine (5.2 g, 0.05 mol) in 100 ml benzene. During the addition, the temperature was allowed to rise to 50° C. and the triethylamine hydrochloride began to precipitate. After the addition was complete, the reaction was stirred an additional 30 minutes. The reaction was filtered and the filtrate evaporated in vacuo to give an oil which crystallized on cooling in an ice bath (m.p. 34°-35° C.). Benzene washings of the material retained on the filter paper gave a second fraction of oil which crystallized on cooling. Total yield was 11.97 g.

Workup

  1. additionDuring the addition
  2. customto rise to 50° C.
  3. customto precipitate
  4. additionAfter the addition
  5. filtrationThe reaction was filtered
  6. customthe filtrate evaporated in vacuo
  7. customto give an oil which
  8. customcrystallized
  9. temperatureon cooling in an ice bath (m.p. 34°-35° C.)
  10. customgave a second fraction of oil which
  11. customcrystallized
  12. temperatureon cooling

Sources & evidence

ORD record
ord-697bb1c229254b88a3c0fbd373c574df
Source dataset
uspto-grants-1988_04
Patent number
US04740600

Linked notes

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