Acetone → 2-(Benzyloxy)-N-methylaniline

HRID 1003243Notes

Reaction equation

HRID 1003243 reaction equation
FC(F)(F)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.CI.CC(C)=O.[OH-].[K+]>CO.O>[CH3:3][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 14797Potassium Hydroxide2×HCID 18796114N-Trifluoroacetyl 2-Benzyloxvaniline

Product 1

HCID 187960752-(Benzyloxy)-N-methylanilineYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
59 °C

Procedure

A well-stirred solution of (25) (0.295 g., 1.0 mM), methyl iodide (0.25 mL, 4.0 mM) and anhydrous acetone (5.0 ml) is set in an oil-bath previously heated to 59° C., and kept for 2 minutes. Powdered anhydrous potassium hydroxide (0.225 g., 4.0 mM) is added all at once, and the bath temperature allowed to rise to 65° C. Clumping-up of some of the KOH is observed. After 15 additional minutes, the reaction mixture is removed from the bath, allowed to cool, and the volatiles removed. Methanol (7 mL) is added with stirring to the residue of N-Methyl-N-trifluoroacetyl-2-benzyloxyaniline (26) obtained, followed by water (1 mL), and methanol (2 mL) (to wash down the sides). After stirring overnight at ambient temperatures, the methanol is removed in vacuo, the residue distributed between ether and water, separated, the organic layer washed with additional water, saturated sodium chloride solution, and dried over sodium sulfate. Concentration of the filtered ether solution gives the title compound (27) (0.212 g.) as an oil. NMR, MS, and TLC indicate little, if any, dimethyl compound.

Workup

  1. customto rise to 65° C
  2. customAfter 15 additional minutes, the reaction mixture is removed from the bath
  3. temperatureto cool
  4. customthe volatiles removed
  5. additionMethanol (7 mL) is added
  6. customobtained
  7. washto wash down the sides)
  8. stirringAfter stirring overnight at ambient temperatures
  9. customthe methanol is removed in vacuo
  10. customseparated
  11. washthe organic layer washed with additional water, saturated sodium chloride solution
  12. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-4073dc733869462095cf1ebe96f7d100
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

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