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

HRID 337365ノート

反応式

HRID 337365 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 867032684-Methoxy-5-methyl-2-nitrophenyl 4-methylbenzenesulfonate収率 81.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4e7cff8f2e564713a42a9ab76bfbd568
出典データセット
uspto-grants-2014_11
特許番号
US08889727B2

反応ノート

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