Potassium Hydroxide → HCID 14495373, compound

HRID 231362Notes

Reaction equation

HRID 231362 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([CH3:13])[C:7]=2[NH2:14])[CH2:5][CH2:4][CH:3]=[CH:2]1.[OH-].[K+]>C(O)(C)C>[C:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([CH3:13])[C:7]=2[NH2:14])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 15664013HCID 15664013, compound

Product 1

HCID 14495373HCID 14495373, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
160 °C

Procedure

A 15.0g (72.61 mmol) portion of 3-(cyclopent-2-enyl)-2,6-toluenediamine was added to a 250cc round bottomed flask containing 1.50g (22.7 mmol) of 85% potassium hydroxide, 16.79 (278.0 mmol) isopropanol, 100cc of mixed xylenes. The mixture was stirred at room temperature under a static nitrogen atmosphere until all the potassium hydroxide had dissolved. The flask was fitted with a Claisen distillation head, a condenser, a receiving flask and then warmed to 115°. Isopropanol and water were removed over a 2 hour period. The temperature of the reaction flask was then raised to 160° C. and maintained for a period of 5 hours. During this period, the mixed xylenes were slowly removed by atmospheric distillation. The product was then isolated from the flask by bulb-to-bulb distillation at 160°-180° C. 10.5mm Hg. An 11.5g sample (76.7% isolated yield) of the α-β-unsaturated product was obtained.

Workup

  1. dissolutionhad dissolved
  2. customThe flask was fitted with a Claisen distillation head, a condenser, a receiving flask
  3. temperaturewarmed to 115°
  4. customIsopropanol and water were removed over a 2 hour period
  5. temperaturemaintained for a period of 5 hours
  6. waitDuring this period
  7. customthe mixed xylenes were slowly removed by atmospheric distillation
  8. customThe product was then isolated from the flask by bulb-to-bulb distillation at 160°-180° C
  9. customAn 11.5g sample (76.7% isolated yield) of the α-β-unsaturated product
  10. customwas obtained

Sources & evidence

ORD record
ord-f1618e320efb4a1fa8da1e94ac6000fc
Source dataset
uspto-grants-1989_07
Patent number
US04845291

Reaction notes

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