Acetic Acid → 4-((3,4,5-Trimethoxybenzyl)sulfinyl)phenol

HRID 357707

반응식

HRID 357707 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][CH:3]=1.C(O)(=[O:24])C>O.[O-2].[O-2].[O-2].[Cr+6]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[O:24])=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 3841364-((3,4,5-Trimethoxybenzyl)thio)phenol

생성물 1

HCID 3841374-((3,4,5-Trimethoxybenzyl)sulfinyl)phenol수율 66%

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 962Water용매2회

반응 조건

온도
80 °C

실험 절차

3,4,5-Trimethoxybenzyl 4-hydroxyphenyl thioether (500 mg, 1.63 mmol), prepared as described in Example 1, was dissolved in 10 mlof acetic acid, and heated to 80° C. A solution of chromium trioxide in 30 ml of distilled water was added dropwise to the above solution. The mixture was stirred for 30 min, cooled to room temperature, diluted with 20 ml of water, and then extracted with 30 ml of ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and purified on silica gel column chromatography (ethyl acetate/n-hexane=1/4) to give 348 mg (66% yield) of 3,4,5-trimethoxybenzyl 4-hydroxyphenyl sulfoxide as a white powder.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with 30 ml of ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified on silica gel column chromatography (ethyl acetate/n-hexane=1/4)

출처 및 근거

ORD 기록
ord-e92c83b6fc5c41b6952ad2903c7a142b
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840991

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