Sodium Iodide → 1-(4-Iodobutyl)-2,3,4,5-tetramethoxy-6-methylbenzene

HRID 1074576노트

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HRID 1074576 반응식
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]O)=[C:7]([CH3:14])[C:6]([O:15][CH3:16])=[C:5]([O:17][CH3:18])[C:4]=1[O:19][CH3:20].C(N(CC)CC)C.CS(Cl)(=O)=O.[I-:33].[Na+]>C(Cl)Cl.CC(C)=O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][I:33])=[C:7]([CH3:14])[C:6]([O:15][CH3:16])=[C:5]([O:17][CH3:18])[C:4]=1[O:19][CH3:20]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20495945HCID 20495945, 화합물

생성물 1

HCID 131875351-(4-Iodobutyl)-2,3,4,5-tetramethoxy-6-methylbenzene수율 94%

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

In anhydrous methylene chloride (300 ml) were 1,2,3,4-tetramethoxy-5-methyl-6-(4-hydroxybutyl)benzene (28.2 g, 0.1 mole) as obtained in Reference Example 59 and triethylamine (16 g, 0.15 mole), and the solution was cooled to 0° C. A solution of methanesulfonyl chloride (14.3 g, 0.12 mole) in methylene chloride (30 ml) was added dropwise to the solution, followed by stirring for 30 minutes. The reaction solution was washed with water, dilute aqueous phosphoric acid and water, successively, and the organic layer was dried (over MgSO4) and freed of the solvent. Acetone (300 ml) and sodium iodide (39.0 g, 0.26 mole) were added to the residue, and the mixture was warmed at 50° C. for 2 hours. After the completion of the reaction, acetone was distilled off under reduced pressure, and isopropyl ether (300 ml) and water (200 ml) were added to the residue for extraction of the product. The organic layer was washed with 5% aqueous sodium hydrosulfite and water, successively, and dried (over MgSO4), followed by distilling off the solvent under reduced pressure. The residue was chromatographed on a column of silica gel, and developing with isopropyl ether-hexane (1:1) yielded 1,2,3,4-tetramethoxy-5-methyl-6-(4-iodobutyl)benzene (37.0 g, 94%).

후처리

  1. washThe reaction solution was washed with water, dilute aqueous phosphoric acid and water
  2. dry with materialsuccessively, and the organic layer was dried (over MgSO4)
  3. temperaturethe mixture was warmed at 50° C. for 2 hours
  4. distillationwas distilled off under reduced pressure, and isopropyl ether (300 ml) and water (200 ml)
  5. additionwere added to the residue for extraction of the product
  6. washThe organic layer was washed with 5% aqueous sodium hydrosulfite and water
  7. dry with materialsuccessively, and dried (over MgSO4)
  8. distillationby distilling off the solvent under reduced pressure
  9. customThe residue was chromatographed on a column of silica gel

출처 및 근거

ORD 기록
ord-09709cc9c2514020aa07095ee09b6647
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04393075

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