Acetamide → HCID 15030057, compound

HRID 359545Notes

Reaction equation

HRID 359545 reaction equation
[CH:1]1([C:7]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[CH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N)(=[O:19])C.[OH-].[K+]>C(O)(=O)C.C(OC(=O)C)(=O)C.C(Cl)Cl.CO>[CH:10]1([C:7]([OH:16])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:19])[CH3:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

8

Reactant 3

HCID 178AcetamideHCID 14797Potassium HydroxideHCID 2319401-cyclohexyl-1-phenylprop-2-yn-1-ol

Product 1

HCID 15030057HCID 15030057, compoundYield 85.6%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 204.8 g (0.95 mole) of 1-cyclohexyl-1-hydroxy-1-phenyl-2-propyne in 1500 mL of acetic acid and 150 mL of acetic anhydride was added 305 g (0.95 mole) of mercuric acetate. The reaction mixture was stirred overnight and then poured into a 3-L round bottomed flask equipped with an overhead stirrer and diluted with 1500 mL of methylene chloride. To this was added 86 g (1.18 mole) of acetamide and 1 L of celite. After being stirred overnight, the mixture was filtered through a large pad of celite. The filtrate washed three times with water twice with a 5% aqueous solution of sodium hydroxide, and once with brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was dissolved in a solution of 76 g (1.14 mole) of potassium hydroxide in 1250 mL of methanol and heated to reflux for 4 hours; the solution was cooled and then poured onto ice. The mixture was extracted four times with methylene chloride. The organic layers were combined, washed four times with water, once with brine, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. Distillation of the residue bulb-to-bulb, bath temperature 100° C. at 0.1 mm Hg, gave 189 g of 1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone, NMR (CDCl3) 1.1-1.4 (m, 6 H), 1.5-1.9 (m, 4 H), 2.1 (s, 3 H), 2.4 (m, 1 H), 4.5 (s, 1 H), 7.2-7.6 (m, 5 H); IR (neat film) 3450, 2925, 2850, 1710, 1490, 1447, 1360 cm-1.

Workup

  1. additionpoured into a 3-L round bottomed flask
  2. customequipped with an overhead stirrer
  3. stirringAfter being stirred overnight
  4. filtrationthe mixture was filtered through a large pad of celite
  5. washThe filtrate washed three times with water twice with a 5% aqueous solution of sodium hydroxide
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent removed under reduced pressure
  8. temperatureheated
  9. temperatureto reflux for 4 hours
  10. temperaturethe solution was cooled
  11. additionpoured onto ice
  12. extractionThe mixture was extracted four times with methylene chloride
  13. washwashed four times with water
  14. dry with materialonce with brine, dried over anhydrous magnesium sulfate
  15. customthe solvent removed under reduced pressure
  16. distillationDistillation of the residue bulb-to-bulb, bath temperature 100° C. at 0.1 mm Hg

Sources & evidence

ORD record
ord-1e77a1b4b4d94e89861bcd74dee2cd17
Source dataset
uspto-grants-1991_03
Patent number
US05001160

Reaction notes

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