Methyl iodide → Methyl 2-[2-(2,5-dimethylphenoxymethyl)phenyl]butyrate

HRID 617389Notes

Reaction equation

HRID 617389 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([CH2:15][CH3:16])[C:13]#N.[OH-:22].[Na+].CI.[C:26](=O)([O-])[O-:27].[K+].[K+]>C(O)C.O>[CH3:1][C:2]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([CH2:15][CH3:16])[C:13]([O:27][CH3:26])=[O:22]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18357786HCID 18357786, compound

Product 1

HCID 18357794Methyl 2-[2-(2,5-dimethylphenoxymethyl)phenyl]butyrateYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]butyronitrile (0.67 g, 2.4 mmol) and 96% sodium hydroxide (0.73 g, 17.5 mmol) in ethanol (8 ml) was heated under reflux for 43 hours. The solvent was evaporated, and then water was added. The mixture was adjusted to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The crude product was dissolved in N,N-dimethylformamide (5 ml) and stirred at room temperature. Methyl iodide (0.50 g, 3.5 mmol) and potassium carbonate (0.50 g, 3.6 mmol) were added thereto in this order. After 1 hour, water was added, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9/1) to give the desired compound methyl 2-[2-(2,5-dimethylphenoxymethyl)phenyl]butyrate (0.62 g, 83%) as white crystals.

Workup

  1. temperatureunder reflux for 43 hours
  2. customThe solvent was evaporated
  3. additionwater was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. dissolutionThe crude product was dissolved in N,N-dimethylformamide (5 ml)
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed successively with water and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated
  12. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-560d73c83ebe403f880970e3d90f5d27
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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