Ethanol → HCID 59721676, compound

HRID 2424268Notes

Reaction equation

HRID 2424268 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]([F:37])([C:33]([F:36])([F:35])[F:34])[CH2:4][C:5]([F:32])([F:31])[CH2:6][C:7]([F:30])([F:29])[CH2:8][CH:9]([C:25]([F:28])([F:27])[F:26])[CH2:10][CH:11]([C:21]([F:24])([F:23])[F:22])[CH2:12][CH:13]([C:17]([F:20])([F:19])[F:18])[CH2:14][CH2:15]I.C(O)C.[S-:43][C:44]#[N:45].[K+]>C(O)(=O)C>[F:1][C:2]([F:39])([F:38])[C:3]([F:37])([C:33]([F:36])([F:35])[F:34])[CH2:4][C:5]([F:32])([F:31])[CH2:6][C:7]([F:30])([F:29])[CH2:8][CH:9]([C:25]([F:28])([F:27])[F:26])[CH2:10][CH:11]([C:21]([F:24])([F:23])[F:22])[CH2:12][CH:13]([C:17]([F:20])([F:19])[F:18])[CH2:14][CH2:15][S:43][C:44]#[N:45]

Participants

5

Reactant 3

HCID 702EthanolHCID 516872Potassium thiocyanateHCID 59721648HCID 59721648, compound

Product 1

HCID 59721676HCID 59721676, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

According to scheme (27) above, in a flask that can be equipped with an agitator, thermocouple and a reflux condenser, 20 grams (27 mmol) of 1,1,1,2,4,4,6,6-octafluoro-2,8,10,12-tetrakis(trifluoromethyl)-14-iodotetradecane (see, e.g. Published Patent Applications), 20 ml of absolute ethanol, 3.9 grams (40.5 mmol) of potassium thiocyanate (KSCN) and 0.5 ml of glacial acetic acid (HOAc) can be placed to form a mixture. The mixture can be heated to reflux (84.7 C) and maintained stirring for overnight. The mixture can be concentrated in vacuo to afford what can be observed as a thick yellow slurry. The slurry can be extracted with 300 ml of diethyl ether and decanted twice and filtered to afford a wet cake and a filtrate. The wet cake can be washed with three 100 ml portions of diethyl ether and the filtrates combined. The combined filtrates can be concentrated in vacuo to afford 17.12 grams (94.6% yield) of the 1,1,1,2,4,4,6,6-octafluoro-2,8,10,12-tetrakis(trifluoromethyl)-14-thiocyanatotetradecane product that can be observed as a light yellow oil. The product structure can be confirmed by NMR and/or chromatographic analysis.

Workup

  1. customcan be equipped with an agitator
  2. customto form a mixture
  3. temperatureThe mixture can be heated
  4. temperatureto reflux (84.7 C)
  5. temperaturemaintained
  6. concentrationThe mixture can be concentrated in vacuo
  7. customto afford what
  8. extractionThe slurry can be extracted with 300 ml of diethyl ether
  9. customdecanted twice
  10. filtrationfiltered
  11. customto afford a wet cake
  12. washThe wet cake can be washed with three 100 ml portions of diethyl ether
  13. concentrationThe combined filtrates can be concentrated in vacuo

Sources & evidence

ORD record
ord-7ebc26d3cfba411295d5d599f73da8a1
Source dataset
uspto-grants-2011_06
Patent number
US07964553B2

Reaction notes

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