Methyl iodide → Methyl 4-methoxyphenylacetate

HRID 48156

반응식

HRID 48156 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15]I>O1CCCC1>[CH3:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

생성물 1

HCID 90266Methyl 4-methoxyphenylacetate수율 83.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of methyl 4-hydroxyphenylacetate (25.0 g, 0.147 mol) in tetrahydrofuran (50 ml) was added dropwise to a stirred suspension of sodium hydride (4.45 g of an 80% dispersion in oil, 0.147 mol) in tetrahydrofuran (150 ml) and the mixture was stirred for 90 minutes. A solution of methyl iodide (20.9 g, 0.47 mol) in tetrahydrofuran (50 ml) was added dropwise and the mixture was stirred overnight at room temperature. The solvent was removed in vacuo, and the residue was partitioned between water and ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel, eluting with ethyl acetate:hexane 1:9, to give methyl 4-methoxyphenylacetate (22.0 g) as a colourless oil.

후처리

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with ethyl acetate:hexane 1:9

출처 및 근거

ORD 기록
ord-b18ace9b66fe460e9a61d18b4777618b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703347B2

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