Ethyl Acetate → HCID 15486935, compound

HRID 1954765Notes

Reaction equation

HRID 1954765 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[CH2:10][C:11]#[N:12].[C:13](OCC)(=[O:15])[CH3:14]>>[C:11]([CH:10]([C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=1[CH3:2])[C:13](=[O:15])[CH3:14])#[N:12]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 1443032,4-DimethylphenylacetonitrileHCID 5360545Sodium

Product 1

HCID 15486935HCID 15486935, compoundYield 74%

Procedure

Sodium pellets (9.8 g, 0.43 mol) were added portionwise to a solution of 2,4-dimethylphenylacetonitrile (48 g, 0.33 mol) in ethyl acetate (150 mL) at ambient temperature. The reaction mixture was heated to reflux temperature and stirred for 16 hours. The resulting suspension was cooled to room temperature and filtered. The collected precipitate was washed with copious amounts of ether and then air-dried. The solid was dissolved in water and a 1N HCl solution was added until the pH=5-6. The mixture was extracted with ethyl acetate (3×200 mL); the combined organic layers were dried over MgSO4 and filtered. Solvent was removed in vacuo to afford a white solid (45.7 g, 74% yield): NMR (CDCl3,300 MHz):; CI-MS: 188 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature
  3. filtrationfiltered
  4. washThe collected precipitate was washed with copious amounts of ether
  5. customair-dried
  6. dissolutionThe solid was dissolved in water
  7. additiona 1N HCl solution was added until the pH=5-6
  8. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  9. dry with materialthe combined organic layers were dried over MgSO4
  10. filtrationfiltered
  11. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-0249931b86f84133be93b0f07d58586e
Source dataset
uspto-grants-2000_09
Patent number
US06124289

Reaction notes

Loading…