Sulfuric Acid → 2-[3-(4-Chlorobenzoyl)isoxazol-5-yl]propionic acid

HRID 638556ノート

反応式

HRID 638556 の反応式
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:12]=[C:11]([CH:13]([CH3:16])[CH2:14][OH:15])[O:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH:19]S(O)(=O)=O>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:12]=[C:11]([CH:13]([CH3:16])[C:14]([OH:19])=[O:15])[O:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 135375952-[3-(4-Chlorobenzoyl)-isoxazol-5-yl]propan-1-ol

生成物 1

HCID 135376032-[3-(4-Chlorobenzoyl)isoxazol-5-yl]propionic acid

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 11.0 g of 2-[3-(4-chlorobenzoyl)-isoxazol-5-yl]propan-1-ol in 1000 ml of CH2Cl2, a few crystals of tetra-n-butylammonium hydrogen sulfate and 150 ml of 9M H2SO4 was added 12.3 g of pulverized K2Cr2O7. The resulting mixture was stirred at room temperature for 1.5 hour. After allowing the mixture to settle, it was decanted from the unreacted dichromate. The aqueous phase was separated and the organics were washed with water and brine, and dried over MgSO4. Concentration of the product gave 8.0 g of a solid. Recrystallization from toluene with norite for decolorizing gave 2.0 g of a solid, m.p. 119°-123°. A second recrystallization from toluene gave 1.6 g (13%) of a solid, m.p. 122.5°-124.5°.

後処理

  1. customit was decanted from the unreacted dichromate
  2. customThe aqueous phase was separated
  3. washthe organics were washed with water and brine
  4. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-6e3a568fd2f04a5bb338565dbdde3e56
出典データセット
uspto-grants-1985_12
特許番号
US04562187

反応ノート

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