Ethanol → (4-Pyridin-2-YL-phenyl)-acetic acid

HRID 1907908Notes

Reaction equation

HRID 1907908 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH2:11]O)=[CH:9][CH:8]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[C-]#N.[K+].[OH-:30].[Na+].[CH2:32]([OH:34])C>C(Cl)Cl.O.CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH2:11][C:32]([OH:34])=[O:30])=[CH:9][CH:8]=1

Participants

10

Reactant 6

HCID 702EthanolHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 1515239(4-(Pyridin-2-yl)phenyl)methanol

Product 1

HCID 504301(4-Pyridin-2-YL-phenyl)-acetic acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The crude of 4-(2-Pyridinyl)benzylalcohol was dissolved in 20 ml DCM, cooled using ice/methanol, triethylamine (1.25 ml, 8.9 mmole) was added followed by methanesulfonylchloride (0.7 ml, 8.9 mmole) added drop wise over 5 minutes. The reaction was allowed to stir at room temperature till the TLC indicated consumption of the starting material (3 hrs), after completion of the reaction, the reaction mixture was washed with water, saturated NaHCO3 solution, and saturated NaCl solution, dried using Na2SO4 and evaporated to produce yellow oil, the oil produced was dissolved in 25 ml of 90% ethanol, KCN (1.05 gm, 16.2 mmole) was then added and it was heated under reflux overnight. Ethanol was evaporated; solid was washed with 50 ml water and filtered. The solid was dissolved in 30 ml of cone. HCl, refluxed for 48 hr; charcoal was added refluxed for 1 hr, filtered. The HCl was evaporated, the solid formed was dissolved in 5 ml of water, NaOH 1 N was added drop wise while extracting with ethyl acetate, the ethyl acetate extract was dried with Na2SO4 and evaporated to produce white solid (0.6 gm, 35% in 3 steps) H1-NMR INOVA-500(DMSO d6) δ 3.641(s, 2H), 7.345(t, J=6.0 Hz, 1H), 7.381(d, J=8.5 Hz, 2H), 7.879(t, J=8.0 Hz, 1H), 7.951(d, J=8.0 Hz, 1H), 8.034(d, J=8.0 Hz, 2H), 8.662(d, J=4.0 Hz, 1H), 12.390(s, 1H).

Workup

  1. temperaturecooled
  2. additionwas added
  3. additionadded drop wise over 5 minutes
  4. customconsumption of the starting material (3 hrs)
  5. customafter completion of the reaction
  6. washthe reaction mixture was washed with water, saturated NaHCO3 solution, and saturated NaCl solution
  7. customdried
  8. customevaporated
  9. customto produce yellow oil
  10. customthe oil produced
  11. temperatureit was heated
  12. temperatureunder reflux overnight
  13. customEthanol was evaporated
  14. washsolid was washed with 50 ml water
  15. filtrationfiltered
  16. dissolutionThe solid was dissolved in 30 ml of cone
  17. temperatureHCl, refluxed for 48 hr
  18. additioncharcoal was added
  19. temperaturerefluxed for 1 hr
  20. filtrationfiltered
  21. customThe HCl was evaporated
  22. customthe solid formed
  23. extractionwhile extracting with ethyl acetate
  24. extractionthe ethyl acetate extract
  25. dry with materialwas dried with Na2SO4
  26. customevaporated
  27. customto produce white solid (0.6 gm, 35% in 3 steps) H1-NMR

Sources & evidence

ORD record
ord-98cc14b2a07f4cf4b1d15aaaaf49ad02
Source dataset
uspto-grants-2013_12
Patent number
US08598169B2

Reaction notes

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