Sodium Hydroxide → HCID 15411100, compound

HRID 1601658Notes

Reaction equation

HRID 1601658 reaction equation
[CH3:1][C:2]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)([CH3:5])[C:3]#[CH:4].[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH3:15][C:10]1[CH:9]=[C:8]([C:7]2[O:16][C:3](=[CH2:4])[C:2]([CH3:1])([CH3:5])[N:6]=2)[CH:13]=[C:12]([CH3:14])[CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15411101HCID 15411101, compound

Product 1

HCID 15411100HCID 15411100, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar, heating mantle, and reflux condenser was added N-(3-methylbutyn-3-yl)-3,5-dimethylbenzamide (25.00 g, 116.1 mmol), 200 mL of toluene, 50 mL of 0.5 N aqueous sodium hydroxide, and 1.74 g (4.31 mmol, 3.7 mol %) of Aliquat® 336. The resulting mixture was heated at reflux for 1.5 h. After cooling, the mixture was transferred to a separatory funnel. The lower aqueous layer was discarded. The organic solution was washed with brine, dried over MgSO4, and filtered. The solution was concentrated using a rotary evaporator to afford a clear colorless oil which was distilled (86-94° C., 0.4 mm) to give 24.43 g (98%) of 2-(3,5-dimethylphenyl)-4,4-dimethyl-5-methyleileoxazoline as a colorless liquid: 1H NMR (400 MHz, CDCl3) δ 7.62 (s, 2H), 7.09 (s, 1H), 4.73 (d, J=3.2 Hz, 1H), 4.22 (d, J=3.2 Hz, 1H), 2.30 (s, 6H), 1.44 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 167.9, 160.1, 138.1, 133.3, 126.7, 125.8, 82.1, 68.9, 29.8, 21.1.

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. temperatureheating mantle
  3. temperaturereflux condenser
  4. temperatureThe resulting mixture was heated
  5. temperatureat reflux for 1.5 h
  6. temperatureAfter cooling
  7. customthe mixture was transferred to a separatory funnel
  8. washThe organic solution was washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationThe solution was concentrated
  12. customa rotary evaporator
  13. customto afford a clear colorless oil which
  14. distillationwas distilled (86-94° C., 0.4 mm)
  15. customto give 24.43 g (98%) of 2-(3,5-dimethylphenyl)-4,4-dimethyl-5-methyleileoxazoline as a colorless liquid

Sources & evidence

ORD record
ord-150a495b71c2451ea458336b7b108ea7
Source dataset
uspto-grants-1999_11
Patent number
US05977368

Reaction notes

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