Potassium Hydroxide → 2-(3-(Prop-1-en-2-yl)phenyl)propan-2-amine

HRID 1707234Notes

Reaction equation

HRID 1707234 reaction equation
[CH3:1][C:2]([N:13]=C=O)([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([CH3:12])=[CH2:11])[CH:5]=1)[CH3:3].[OH-].[K+]>C(O)(C)C>[CH3:3][C:2]([NH2:13])([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([CH3:12])=[CH2:11])[CH:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

Product 1

HCID 147165412-(3-(Prop-1-en-2-yl)phenyl)propan-2-amineYield 88.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

13.6 g of 1-methyl-1-[3-(1-methylethenyl)phenyl]ethyl isocyanate were dissolved in 30 ml of isopropyl alcohol, and 19.0 g of potassium hydroxide were then added to the solution, followed by stirring for 3 hours under heating and reflux. Afterward, the solution was concentrated under reduced pressure, and then poured into ice water. After extraction with dichloromethane, the resultant extract was dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure again to obtain 10.5 g of 1-methyl-1-[3-(1-methylethenyl)phenyl]ethylamine.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. concentrationAfterward, the solution was concentrated under reduced pressure
  4. additionpoured into ice water
  5. extractionAfter extraction with dichloromethane
  6. extractionthe resultant extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationThe solution was concentrated under reduced pressure again

Sources & evidence

ORD record
ord-69fb8a0cd222498386a29ad8feb8ac34
Source dataset
uspto-grants-1994_10
Patent number
US05352655

Reaction notes

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