Pyridine → HCID 69308958, compound

HRID 2055762Notes

Reaction equation

HRID 2055762 reaction equation
CN(C=O)C.S(Cl)([Cl:8])=O.N1C=CC=CC=1.[CH2:16]([O:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:36]=1)[CH2:32]O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>ClCCl>[CH2:16]([O:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:36]=1)[CH2:32][Cl:8])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 58788077[3,5-Bis(dodecyloxy)phenyl]methanol

Product 1

HCID 69308958HCID 69308958, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 L RBF was prepared containing 5 mL dry dichloromethane, a stir bar, a septum, an out-vent line, and a nitrogen gas line. DMF (3.3 ml, 40.3 mmol) was added and the reaction mixture was cooled in an ice bath. Thionyl chloride (2.7 ml, 40.3 mmol) was added and the reaction mixture was allowed to stir for 10 minutes. The ice bath was then removed and the reaction was allowed to stir for an additional 10 minutes. The RBF was placed in the ice bath and a mixture of pyridine (2.72 ml, 33.6 mmol) and 3,5-didodecoxybenzyl alcohol (13.2 g, 33.6 mmol) were added and dissolved in approximately 50 mL dichloromethane, drop-wise through the septum. After 15 minutes, the RBF was removed from the ice bath and the reaction mixture was stirred for 2 hours. The reaction mixture was then placed in a refrigerator overnight. The solvent was removed by rotary evaporation. To the remaining organic matter, 100 mL of 50% ether/hexanes was added to dissolve the desired derivative. A solid orange precipitate formed, the remaining liquid was decanted off, and the precipitate was washed with an additional 100 mL 50% ether/hexanes. The combined organic liquid was vacuum filtered through silica gel into a RBF and the solvent was removed under reduced pressure. Trace solvent was removed by high vacuum overnight. There was a 10.2 g yield or a 88.5% yield. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.87 (t, J=6.6, 6H, CH2CH3), 1.15-1.6 (m, 36H, CH2(CH2)9), 1.76 (p, J=8.0, 4H, OCH2CH2), 3.9 (t, J=6.6, 4H, OCH2CH2), 4.5 (s, 2H, ArCH2), 6.36 (t, J=2.2, 1H, ArH), 6.50 (d, J=2.2, 2H, ArH).

Workup

  1. customA 1 L RBF was prepared
  2. temperaturethe reaction mixture was cooled in an ice bath
  3. customThe ice bath was then removed
  4. stirringto stir for an additional 10 minutes
  5. additionwere added
  6. waitAfter 15 minutes
  7. customthe RBF was removed from the ice bath
  8. stirringthe reaction mixture was stirred for 2 hours
  9. customwas then placed in a refrigerator overnight
  10. customThe solvent was removed by rotary evaporation
  11. additionTo the remaining organic matter, 100 mL of 50% ether/hexanes was added
  12. dissolutionto dissolve the desired derivative
  13. customA solid orange precipitate formed
  14. customthe remaining liquid was decanted off
  15. washthe precipitate was washed with an additional 100 mL 50% ether/hexanes
  16. filtrationfiltered through silica gel into a RBF
  17. customthe solvent was removed under reduced pressure
  18. customTrace solvent was removed by high vacuum overnight
  19. customyield

Sources & evidence

ORD record
ord-f0dd24957ea64f8ca3b4a06fd84d69de
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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