Methanol → 2-(4-Cyclopropylphenyl)acetic acid

HRID 1913422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913422
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.CO.[OH-].[Na+]>C1COCC1>[CH:11]1([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:14])=[O:2])=[CH:6][CH:7]=2)[CH2:12][CH2:13]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66845395Methyl(4-cyclopropylphenyl)acetate

Produkt 1

HCID 204905282-(4-Cyclopropylphenyl)acetic acidAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl(4-cyclopropylphenyl)acetate (710 mg, 3.73 mmol) was dissolved in 5 mL THF, 5 mL MeOH, and aqueous 1N NaOH (7.46 mmol) and the resulting mixture was heated at 45° C. overnight. After cooling to ambient temperature, the reaction was concentrated in vacuo and the residue was diluted with water (50 mL). The aqueous material was acidified with 1N HCl to pH˜3. A light brown precipitate formed which was collected by filtration and dried in a vacuum oven for 3 days to give (4-cyclopropylphenyl)acetic acid (SM-1ag, 395 mg, 60%). MS (ES−) 175.2 (M−H). 1H NMR (DMSO-d6) δ 0.57-0.61 (m, 2H), 0.86-0.91 (m, 2H), 1.81-1.88 (m, 1H), 3.45 (s, 2H), 6.97 (d, 2H), 7.08 (d, 2H), 12.20 (br s, 1H).

Aufarbeitung

  1. concentrationthe reaction was concentrated in vacuo
  2. additionthe residue was diluted with water (50 mL)
  3. customA light brown precipitate formed which
  4. filtrationwas collected by filtration
  5. customdried in a vacuum oven for 3 days

Quellen und Nachweise

ORD-Eintrag
ord-c04158598db546e0a6dd933494e36fb3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609680B2

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