Potassium Carbonate → 4-((3,4,5-Trimethoxybenzyl)thio)phenol

HRID 357705

反応式

HRID 357705 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:20]Br>CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:20][C:19]2[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:17]([O:16][CH3:15])[CH:18]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 103552715-(Bromomethyl)-1,2,3-trimethoxybenzene

生成物 1

HCID 3841364-((3,4,5-Trimethoxybenzyl)thio)phenol収率 68.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

4-Hydroxy thiophenol (12 g, 0.095 mol) and potassium carbonate (15.86 g, 0.115 mol) were dissolved in 250 ml of N,N-dimethylformamide, and cooled to 0° C. To the above solution at 0° C. was added dropwise 25 g (0.095 mol) of 3,4,5-trimethoxybenzyl bromide prepared in step (1) dissolved in 50 ml N,N-dimethylformamide. After stirring for 2 hr, the ice-bath was removed, and the solution was stirred overnight. The whole solution was poured into water, and extracted with 300 ml ethyl acetate. The organic layer was washed twice with 300 ml of water. Drying over magnesium sulfate, filtration, concentration, and chromatographic purification on silica gel column (ethyl acetate/n-hexane=2/3) gave 20 g (yield 68%) of 3,4,5-trimethoxybenzyl 4-hydroxyphenyl thioether as a white solid.

後処理

  1. customthe ice-bath was removed
  2. stirringthe solution was stirred overnight
  3. additionThe whole solution was poured into water
  4. extractionextracted with 300 ml ethyl acetate
  5. washThe organic layer was washed twice with 300 ml of water
  6. dry with materialDrying over magnesium sulfate, filtration, concentration, and chromatographic purification on silica gel column (ethyl acetate/n-hexane=2/3)

出典と根拠

ORDレコード
ord-577d302a667c416aaa4696872b29ad7f
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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