Potassium Iodide → 2-Methyl-3-(3-methyl-2-nitrophenoxy)-1-propene

HRID 52661

Reaction equation

HRID 52661 reaction equation
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19](=[CH2:21])[CH3:20].[I-].[K+]>CS(C)=O.O>[CH3:20][C:19]([CH2:21][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N+:9]([O-:11])=[O:10])=[CH2:18]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 210263-Methyl-2-nitrophenol

Product 1

HCID 108222032-Methyl-3-(3-methyl-2-nitrophenoxy)-1-propeneYield 100.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 20.0 grams (0.130 mole) of 3-methyl-2-nitrophenol and 22.5 grams (0.163 mole) of potassium carbonate in 200 mL of dimethyl sulfoxide was stirred, and 15.3 mL (0.156 mole) of methallyl chloride was added dropwise during a five minute period. Upon completion of addition, 5.4 grams (0.033 mole) of potassium iodide was added in one portion. The reaction mixture was then stirred at ambient temperature for about 18 hours. After this time the reaction mixture was poured into 500 mL of water. The mixture was then extracted with two 200 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 27.0 grams of 2-methyl-3-(3-methyl-2-nitrophenoxy)-1-propene. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added in one portion
  2. stirringThe reaction mixture was then stirred at ambient temperature for about 18 hours
  3. extractionThe mixture was then extracted with two 200 mL portions of diethyl ether
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd9f1a1798ea4d10a84f8507f2850373
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Linked notes

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