Triethylamine → beta-Nitrocinnamyl Perfluorooctanoate

HRID 1633188Notes

Reaction equation

HRID 1633188 reaction equation
[N+:1]([C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH:5][CH2:6][OH:7])([O-:3])=[O:2].C(N(CC)CC)C.[F:21][C:22]([F:45])([C:26]([F:44])([F:43])[C:27]([F:42])([F:41])[C:28]([F:40])([F:39])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])[C:23](Cl)=[O:24]>C1(C)C=CC=CC=1.CCOCC.C(O)C>[F:21][C:22]([F:45])([C:26]([F:43])([F:44])[C:27]([F:41])([F:42])[C:28]([F:39])([F:40])[C:29]([F:37])([F:38])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])[C:23]([O:7][CH2:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:24]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 78978Perfluorooctanoyl chlorideHCID 54473650beta-Nitrocinnamyl alcohol

Product 1

HCID 53639101beta-Nitrocinnamyl Perfluorooctanoate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

β-Nitrocinnamyl alcohol (5.4 g, 0.03 mol) and one equivalent of triethylamine (3.03 g, 0.03 mol) were dissolved in 100 M of toluene. The solution was cooled in an ice bath and perfluorooctanoyl chloride (2.6 g, 0.03 mol) was added dropwise with stirring. The reaction was stirred an addtional two hours and diluted with ether. The reaction was extracted with water and the organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The oily product was crystallized from petroleum ether to give yellow prisms, mp 79-81°, IR 1785, 1655, 1535, 1325, and 1200 cm-1. A solution of the material in 95% ethanol showed an absorption of λmax at 302 nm, epsilon=10,800 which rapidly decreased on exposure to the GE H3T7 source. This loss of the 302 nm absorption was accompanied by a decrease in the pH (increased acidity) of the solution as as indicated by methyl red pH indicator.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. stirringThe reaction was stirred an addtional two hours
  3. extractionThe reaction was extracted with water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe oily product was crystallized from petroleum ether
  7. customto give yellow prisms, mp 79-81°, IR 1785, 1655, 1535, 1325, and 1200 cm-1
  8. customan absorption of λmax at 302 nm, epsilon=10,800 which
  9. customThis loss of the 302 nm absorption
  10. temperaturewas accompanied by a decrease in the pH (increased acidity) of the solution as

Sources & evidence

ORD record
ord-d3e8950b13bb47d088070983be7843b2
Source dataset
uspto-grants-1984_10
Patent number
US04478967

Reaction notes

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