Methyl iodide → 3-Methoxy-2-methylbenzonitrile

HRID 1389511Notes

Reaction equation

HRID 1389511 reaction equation
[OH:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:11](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:10][C:3]1[C:2]([O:1][CH3:11])=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 226160943-Hydroxy-2-methylbenzonitrile

Product 1

HCID 110947703-Methoxy-2-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-hydroxy-2-methylbenzonitrile [23.38 g described by S. Gabriel and A. Thieme, Ber., 52, 1079 (1919)] anhydrous potassium carbonate (26.7 g) and methyl iodide (16.43 ml) in acetone (255 ml) is refluxed for 4 hr, cooled and filtered. The filtrate is evaporated and dissolved in dichloromethane. The solution is washed with water, dried and evaporated. The residue is chromatographed on silica gel using dichloromethane-hexane(1:1) and the eluates are evaporated and crystallized from hexane to obtain 2-methyl-3-methoxybenzonitrile: (II: R1 =2-Me and Y=CN): mp 47°-48° C.; ir 2,220, 1,265 and 1,100 cm-1 ; and nmr (CDCl3) δ2.42 (s, 3H), 3.85 (s, 3H) and 7.15 (m, 3H).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. dissolutiondissolved in dichloromethane
  5. washThe solution is washed with water
  6. customdried
  7. customevaporated
  8. customThe residue is chromatographed on silica gel
  9. customthe eluates are evaporated
  10. customcrystallized from hexane

Sources & evidence

ORD record
ord-3c3335c7bd4741fe93febaaab1a89a19
Source dataset
uspto-grants-1981_01
Patent number
US04244966

Reaction notes

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