1-(p-Tolyl)cyclopropanecarboxylic acid → Methyl 1-(p-tolyl)cyclopropanecarboxylate

HRID 332679

反応式

HRID 332679 の反応式
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:15])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 986391-(p-Tolyl)cyclopropanecarboxylic acidHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylate収率 969.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

To a stirred solution of 1-(p-tolyl)cyclopropanecarboxylic acid (6 g, 34.05 mmol) in methanol (48 mL), was added para-toluenesulphonic acid monohydrate (0.648 g, 3.405 mmol). The reaction was stirred at 75° C. for 16 hours. The mixture was concentrated under reduced pressure, and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine and dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford the title compound as an orange oil (6.279 g, 97%). The material was used directly in the next step with no further purification.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fe34e0c1a34e4020bb1a957d88d61f8d
出典データセット
uspto-grants-2014_11
特許番号
US08877774B2

関連ノート

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