1-(4-Methoxyphenyl)cyclopropane-1-carboxylic acid → Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylate

HRID 401519

反応式

HRID 401519 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:16][O:13][C:12]([C:9]1([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)=[O:14]

参加物

4

反応物 2

HCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 13707544Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylate収率 1,995.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid (50.0 g, 0.26 mol) in MeOH (500 mL) was added toluene-4-sulfonic acid monohydrate (2.5 g, 13 mmol) at room temperature. The reaction mixture was heated at reflux for 20 hours. MeOH was removed by evaporation under vacuum and EtOAc (200 mL) was added. The organic layer was washed with sat. aq. NaHCO3 (100 mL) and brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester (53.5 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 7.25-7.27 (m, 2H), 6.85 (d, J=8.8 Hz, 2H), 3.80 (s, 3H), 3.62 (s, 3H), 1.58 (m, 2H), 1.15 (m, 2H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 hours
  3. customMeOH was removed by evaporation under vacuum and EtOAc (200 mL)
  4. additionwas added
  5. washThe organic layer was washed with sat. aq. NaHCO3 (100 mL) and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under vacuum

出典と根拠

ORDレコード
ord-2b639f3d87124ebd92af3cab078cca79
出典データセット
uspto-grants-2014_06
特許番号
US08741933B2

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