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

HRID 357707

反応式

HRID 357707 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 10219390chromium (VI) trioxide触媒HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e92c83b6fc5c41b6952ad2903c7a142b
出典データセット
uspto-grants-1998_11
特許番号
US05840991

関連ノート

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