Triethylamine → HCID 54186085, compound

HRID 1708857Notes

Reaction equation

HRID 1708857 reaction equation
[CH:1]([CH:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].ClCC=CC1C=CC=CC=1.C(N(CC)CC)C.[F:28][C:29]([F:48])([C:33]([F:47])([F:46])[C:34]([F:45])([F:44])[C:35]([F:43])([F:42])[C:36]([F:41])([F:40])[CH:37]([F:39])[F:38])[C:30](Cl)=[O:31]>C(OCC)C>[CH:1]([CH:3]([O:10][C:30](=[O:31])[C:29]([F:28])([F:48])[C:33]([F:46])([F:47])[C:34]([F:44])([F:45])[C:35]([F:42])([F:43])[C:36]([F:40])([F:41])[CH:37]([F:38])[F:39])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 92986alpha-Vinylbenzyl alcoholHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 27761327H-Perfluoroheptanoyl chloride

Product 1

HCID 54186085HCID 54186085, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

100 ml of diethyl ether, 40.2 g (0.3 mol) of vinylbenzylalcohol (synthesized by the method described in "Polymer", 14 330 (1973) from chloromethylstyrene (meta: para=about 6: about 4); b.p.=69° to 73° C./0.4 mm Hg), 30.3 g (0.3 mol) of triethylamine, and 0.5 g of 2,6-di-tbutylphenol were charged into a 300-ml three-necked flask equipped with a stirrer, a reflux condenser, and a calcium chloride tube, and the mixture was then cooled with ice-water. 109.4 g (0.3 mol) of the 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-n-heptanoic acid chloride synthesized above was cooled with ice and was added to the mixture dropwise, with stirring. Next the mixture was stirred for 2 hours at room temperature, after which it was stirred for 1 hour under reflux. Then, after cooling, the deposited triethylamine hydrochloride was filtered off, the filtrate was washed twice with water, then with an aqueous sodium carbonate solution, and then it was dried over anhydrous sodium carbonate. Distillation was carried out twice to purify the dried filtrate, thus giving 61.0 g (yield: 44.0%; b.p.: 106 to 116° C./0.9 mm Hg; d: 1.47) of 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-n-heptanoic acid vinylbenzyl ester.

Workup

  1. customequipped with a stirrer, a reflux condenser, and a calcium chloride tube
  2. temperatureabove was cooled with ice
  3. additionwas added to the mixture dropwise
  4. stirringNext the mixture was stirred for 2 hours at room temperature
  5. stirringafter which it was stirred for 1 hour
  6. temperatureunder reflux
  7. temperatureThen, after cooling
  8. filtrationthe deposited triethylamine hydrochloride was filtered off
  9. washthe filtrate was washed twice with water
  10. dry with materialwith an aqueous sodium carbonate solution, and then it was dried over anhydrous sodium carbonate
  11. distillationDistillation
  12. customto purify the dried filtrate

Sources & evidence

ORD record
ord-d74d3fabd4504b3683ed5d29e9c3753c
Source dataset
uspto-grants-1990_08
Patent number
US04946771

Reaction notes

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