p-Toluenesulfonic acid → Methyl 1-phenylcyclopropane-1-carboxylate

HRID 503278

反応式

HRID 503278 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.[CH3:13]C1C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>CO>[C:1]1([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 802061-Phenylcyclopropanecarboxylic acid

生成物 1

HCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate収率 147.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 1-phenylcyclopropanecarboxylic acid (25 g, 0.15 mol) in CH3OH (200 mL) was added TsOH (3 g, 0.1 mol) at room temperature. The mixture was refluxed overnight. The solvent was evaporated under reduced pressure to give crude product, which was dissolved into EtOAc. The EtOAc layer washed with aq. sat. NaHCO3. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to give methyl 1-phenylcyclopropanecarboxylate (26 g, 96%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 7.37-7.26 (m, 5H), 3.63 (s, 3H), 1.63-1.60 (m, 2H), 1.22-1.19 (m, 2H).

後処理

  1. temperatureThe mixture was refluxed overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customto give crude product, which
  4. washThe EtOAc layer washed with aq. sat. NaHCO3
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-983aea54acea40789ee87e0e1c273d96
出典データセット
uspto-grants-2010_08
特許番号
US07776905B2

関連ノート

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