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

HRID 468285

反応式

HRID 468285 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 was 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 was washed
  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-29c52934380345bba7ca297633c1d783
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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