Sulfuric Acid → 1-(4-Iodophenyl)cyclopropane-1-carboxylic acid

HRID 1274261

反応式

HRID 1274261 の反応式
[C:1]1([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:13]([O-])(=O)=O.[Na+].S(=O)(=O)(O)O>C(O)(=O)C>[I:13][C:4]1[CH:5]=[CH:6][C:1]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:2][CH:3]=1

参加物

5

反応物 3

HCID 1118Sulfuric Acid2 回HCID 802061-Phenylcyclopropanecarboxylic acidHCID 23675764Sodium Iodate2 回

生成物 1

HCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acid収率 106%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

A mixture of 1-phenylcyclopropane carboxylic acid (16.5 g, 101 mmol), sodium iodate (5.04 g) and concentrated sulfuric acid (1 mL) in acetic acid (70 mL) was stirred and heated at 70° C. for 2 days. Additional sodium iodate (1.88 g) and sulfuric acid (1 mL) were added, and stirring was continued for 1 day. The acetic acid was evaporated, and the residue was partitioned between ethyl acetate and water. The organic phase was washed with aqueous sodium thiosulfate, dried, filtered, and evaporated. The solid residue was recrystallized form methanol/water to give 1-(4-iodophenyl)cyclopropane-1-carboxylic acid (7.98 g, 27 mmol, 27%).

後処理

  1. stirringstirring
  2. customThe acetic acid was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with aqueous sodium thiosulfate
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue was recrystallized form methanol/water

出典と根拠

ORDレコード
ord-0c1b33025f2e4dde9efd613106d3b064
出典データセット
uspto-grants-2000_12
特許番号
US06156784

関連ノート

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