Water → 4-Hydroxy-3,5-dimethoxybenzyl 4-hydroxyphenyl thioether

HRID 357709

反応式

HRID 357709 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]C)=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][CH:3]=1.O>C(Cl)Cl>[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]([OH:18])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 962WaterHCID 3841364-((3,4,5-Trimethoxybenzyl)thio)phenol

生成物 1

HCID 158403984-Hydroxy-3,5-dimethoxybenzyl 4-hydroxyphenyl thioether収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

3,4,5-Trimethoxybenzyl 4-hydroxyphenyl thioether (3 g, 9.8 mmol), prepared as described in Example 1, was dissolved in 60 ml of dry methylene chloride, and cooled to -78° C. A solution of borontribromide (2.8 ml, 29.5 mmol) in 10 ml of methylene chloride was added dropwise to the above solution. The mixture was stirred to room temperature, and immediately cooled to 0° C. Water (50 ml) was then added dropwise, and the methylene chloride layer was separated. The crude product, obtained after being dried over magnesium sulfate and concentrated, was purified on silica gel column chromatography (ethyl acetate/n-hexane=1/2) to give 1.8 g (63% yield) of 4-hydroxy-3,5-dimethoxybenzyl 4-hydroxyphenyl thioether as a white solid.

後処理

  1. temperatureimmediately cooled to 0° C
  2. customthe methylene chloride layer was separated
  3. customThe crude product, obtained
  4. dry with materialafter being dried over magnesium sulfate
  5. concentrationconcentrated
  6. customwas purified on silica gel column chromatography (ethyl acetate/n-hexane=1/2)

出典と根拠

ORDレコード
ord-452f5651b20a4cdf9b9505d7bd5ee1a0
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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