4-Toluenesulfonyl chloride → 1-[(4-Methyl-phenyl)-sulfonyloxy]-3,4-dihydroxy benzene

HRID 1614722

反応式

HRID 1614722 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[OH:9].[H-].[Na+].B(OCC)(OCC)OCC.[S:22](Cl)([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>CN(C)C=O.C(OCC)(=O)C>[CH3:29][C:28]1[CH:30]=[CH:31][C:25]([S:22]([O:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([OH:9])[CH:4]=2)(=[O:24])=[O:23])=[CH:26][CH:27]=1

参加物

7

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 9009Triethyl borateHCID 107871,2,4-BenzenetriolHCID 24758Sodium hydride

生成物 1

HCID 197725271-[(4-Methyl-phenyl)-sulfonyloxy]-3,4-dihydroxy benzene収率 50.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

1.37 g of 1,2,4-trihydroxy benzene and 40 ml of anhydrous dimethylformamide were mixed together under an inert gas atmosphere and then 0.984 g of sodium hydride in suspension at 53% in oil were added slowly at 15°-20° C. The mixture was stirred for one hour and then 1.906 ml of triethyl borate were added, followed by stirring for one hour. Then, a solution of 2.072 g of tosyl chloride in 15 ml of dimethylformamide were added over 2 hours and the mixture was stirred for 4 hours at ambient temperature. The mixture was poured into a water-ice-hydrochloric acid mixture and extraction took place with ethyl acetate followed by evaporating to dryness. The crude residue was washed with petroleum ether and after chromatography on silica and eluting with a cyclohexane-ethyl acetate (1-1) mixture, 1.53 g of the expected product were obtained which was crystallized from a flugene-isopropyl ether mixture.

後処理

  1. stirringby stirring for one hour
  2. stirringthe mixture was stirred for 4 hours at ambient temperature
  3. customby evaporating to dryness
  4. washThe crude residue was washed with petroleum ether
  5. washafter chromatography on silica and eluting with a cyclohexane-ethyl acetate (1-1) mixture

出典と根拠

ORDレコード
ord-a930ef55b2d948f3a011b0fb40d92a05
出典データセット
uspto-grants-1993_03
特許番号
US05198571

関連ノート

読み込み中…