Methanol → 1-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acid

HRID 2068525ノート

反応式

HRID 2068525 の反応式
[CH2:1]([O:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12]2)=[O:9])=[CH:6][CH:5]=1)[CH3:2].O1CCCC1.CO.[OH-].[Li+]>O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)=[O:9])=[CH:19][CH:20]=1)[CH3:2]

参加物

6

反応物 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58304093Ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate

生成物 1

HCID 583041121-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acid収率 99.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

Add ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate (478 g, 1.72 mol) to tetrahydrofuran (2 L) and methanol (1 L). Dissolve lithium hydroxide (LiOH) (144.7 g, 3.45 mol) in water (1 L) and add it to the mixture. Stir the reaction mixture while heating to 55° C. Cool the reaction to ambient temperature and concentrate under reduced pressure. After removing 2.5 L of solvent, dilute the mixture with water (2 L) and immerse it in an ice water bath. Adjust to pH 2 with aqueous 5N hydrochloric acid (750 mL). Filter the precipitate, wash the cake with water (2×2 L), and dry to give the title compound (425 g, 99%) as a white powder: MS (m/z): 250 (M+1).

後処理

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. concentrationconcentrate under reduced pressure
  4. customAfter removing 2.5 L of solvent
  5. additiondilute the mixture with water (2 L)
  6. filtrationFilter the precipitate
  7. washwash the cake with water (2×2 L)
  8. customdry

出典と根拠

ORDレコード
ord-96efa7d14b8349d7a7def82f7dd0264d
出典データセット
uspto-grants-2012_10
特許番号
US08299061B2

反応ノート

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