Methyl iodide → Methyl 2-(methoxyimino)-2-(2-methylphenyl)acetate

HRID 1885728Notes

Reaction equation

HRID 1885728 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[N:13]([O:15][C:16](C)(C)C)=O.[K].CI>C(O)(C)(C)C.C(O)(C)C.O>[CH3:16][O:15][N:13]=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[C:9]([O:11][CH3:12])=[O:10]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 10906Tert-Butyl nitriteHCID 5462222Potassium2×HCID 7021479Methyl 2-(2-methylphenyl)acetate

Product 1

HCID 54500888Methyl 2-(methoxyimino)-2-(2-methylphenyl)acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6386tert-ButanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 200 g (1.22 mol) of methyl 2-methylphenylacetate and 377 g (3.66 mol) of tert.-butyl nitrite in 400 ml of tert.-butanol is added rapidly to 150 g (1.34 mol) of potassium tert.-butylate in 1500 ml of anhydrous tert.-butanol, the reaction temperature increasing to 70° C. After a few minutes, the potassium salt which forms begins to precipitate, and the reaction solution becomes difficult to stir. The mixture is stirred for a further one hour, and 261 g (1.84 mol) of methyl iodide are added in one portion. The potassium salt slowly dissolves, and microcrystalline potassium iodide precipitates. The mixture is stirred at room temperature overnight and evaporated, the residue is taken up in methyl tert.-butyl ether/H2O, and the solution is washed several times with H2O, dried over sodium sulfate and re-evaporated. The residue obtained is dissolved in warm isopropanol. H2O is added until the turbidity has just disappeared, and the product is then allowed to crystallize out at 0° C. 114 g (45%, m.p. =65°-66° C.) of product are obtained.

Workup

  1. waitAfter a few minutes
  2. customto precipitate
  3. stirringThe mixture is stirred for a further one hour
  4. custommicrocrystalline potassium iodide precipitates
  5. stirringThe mixture is stirred at room temperature overnight
  6. customevaporated
  7. washthe solution is washed several times with H2O
  8. dry with materialdried over sodium sulfate
  9. customre-evaporated
  10. customThe residue obtained
  11. customto crystallize out at 0° C
  12. custom114 g (45%, m.p. =65°-66° C.) of product are obtained

Sources & evidence

ORD record
ord-74e6dd1e563b4995a93dd5fade0c7989
Source dataset
uspto-grants-1992_09
Patent number
US05145980

Reaction notes

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