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

HRID 503278

Reaktionsgleichung

Reaktionsgleichung von HRID 503278
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 12861006Methyl 1-phenylcyclopropane-1-carboxylateAusbeute 147,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-983aea54acea40789ee87e0e1c273d96
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776905B2

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