Sodium Iodide → 2-Methoxy-4-propylphenyl 4-methylbenzenesulfonate

HRID 625990

반응식

HRID 625990 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[OH:12].[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(#N)C>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:12][C:4]2[CH:5]=[CH:6][C:7]([CH2:9][CH2:10][CH3:11])=[CH:8][C:3]=2[O:2][CH3:1])(=[O:23])=[O:22])=[CH:25][CH:26]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 177394-Propylguaiacol

생성물 1

HCID 591913892-Methoxy-4-propylphenyl 4-methylbenzenesulfonate수율 66%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

To a solution of 2-methoxy-4-propylphenol (10.0 mmol; 1.6 mL), NaI (1.0 mmol; 150 mg), and K2CO3 (11.0 mmol; 1.52 g), under argon, in acetonitrile (20 mL) was added tosyl chloride (10.5 mmol; 2.0 g). The reaction mixture was stirred at 70° C. for 36 hr, then quenched with NaOH (0.1N; 3 mL), and extracted with ethyl acetate (2*10 mL). Combined organic phases were washed with saturated NaHCO3 sat. (5 mL), dried over MgSO4, concentrated in vacuo. The crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane) to yield the desired compound as a clear oil (2.13 g; 6.6 mmol; 66%).

후처리

  1. customquenched with NaOH (0.1N; 3 mL)
  2. extractionextracted with ethyl acetate (2*10 mL)
  3. washCombined organic phases were washed with saturated NaHCO3 sat. (5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane)

출처 및 근거

ORD 기록
ord-3cc95fae80bc4f42afe4dcfdc47233ef
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309179B2

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