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

HRID 427992노트

반응식

HRID 427992 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-62b8a2a21d4a4c76b32620f9b47214a1
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313150B1

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