Water → 4-Methoxy-5-methyl-2-nitrophenyl 4-methylbenzenesulfonate

HRID 337365

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HRID 337365 반응식
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([OH:10])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:10][C:6]2[CH:7]=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])(=[O:22])=[O:21])=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 574186644-Methoxy-5-methyl-2-nitrophenol

생성물 1

HCID 867032684-Methoxy-5-methyl-2-nitrophenyl 4-methylbenzenesulfonate수율 81.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 4-methoxy-5-methyl-2-nitro phenol (8.0 g) in methylene chloride (80 mL) was added p-toluenesulfonyl chloride (9.15 g) at room temperature under nitrogen atmosphere. The mixture was cooled to 0° C. To this mixture triethylamine (4.86 g) was added and stirred for 2 h. Then the reaction mixture was poured into water (150 mL) and extracted with methylene chloride (150 mL). The organic layer was washed with water (100 mL) and saturated brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (9:1) to give the title compound (12.0 g).

후처리

  1. extractionextracted with methylene chloride (150 mL)
  2. washThe organic layer was washed with water (100 mL) and saturated brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel

출처 및 근거

ORD 기록
ord-4e7cff8f2e564713a42a9ab76bfbd568
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889727B2

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