1-(p-Tolyl)cyclopropanecarboxylic acid → Methyl 1-(p-tolyl)cyclopropanecarboxylate

HRID 332679

Reaktionsgleichung

Reaktionsgleichung von HRID 332679
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:15])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 986391-(p-Tolyl)cyclopropanecarboxylic acidHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylateAusbeute 969,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a stirred solution of 1-(p-tolyl)cyclopropanecarboxylic acid (6 g, 34.05 mmol) in methanol (48 mL), was added para-toluenesulphonic acid monohydrate (0.648 g, 3.405 mmol). The reaction was stirred at 75° C. for 16 hours. The mixture was concentrated under reduced pressure, and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine and dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford the title compound as an orange oil (6.279 g, 97%). The material was used directly in the next step with no further purification.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fe34e0c1a34e4020bb1a957d88d61f8d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

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