Sodium Hydroxide → 4'-Methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid

HRID 1845158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845158
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[C:10]([C:18]([O:20]C)=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:11]=[C:10]([C:18]([OH:20])=[O:19])[CH:9]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58188120Methyl 4'-methyl-5-(methylsulfonyl)biphenyl-3-carboxylate

Produkt 1

HCID 581879934'-Methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of methyl 4′-methyl-5-(methylsulfonyl)biphenyl-3-carboxylate (0.55 g, 1.8 mmol), MeOH (50 mL) and 2N aq. NaOH (4 mL) was stirred at 50° C. for 3 h. After cooling the mixture was concentrated in vacuo and acidified with 1N aq. HCl to pH<4 and extracted with EtOAc (100 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated to yield a white solid. LC-MS: 289.3 [M−1]−; 1H NMR (400 MHz, CDCl3): δ 8.61 (t, 1H, J=1.6 Hz), 8.59 (t, 1H, J=1.6 Hz), 8.39 (t, 1H, J=1.6 Hz), 7.58 (d, 2H, J=8.0 Hz), 7.33 (d, 2H, J=8.0 Hz), 3.15 (s, 3H), 2.44 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. concentrationwas concentrated in vacuo
  3. extractionextracted with EtOAc (100 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto yield a white solid

Quellen und Nachweise

ORD-Eintrag
ord-c810698803004d59816ecf75ada8efb9
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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