Potassium Hydroxide → 3-(4-Phenylphenyl)prop-2-enoic acid

HRID 29691

Reaktionsgleichung

Reaktionsgleichung von HRID 29691
C[O:2][C:3](=[O:18])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[C:9]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[CH:11][C:6]([CH:5]=[CH:4][C:3]([OH:18])=[O:2])=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 692086043-Biphenyl-4-yl-acrylic acid methyl ester

Produkt 1

HCID 254923-(4-Phenylphenyl)prop-2-enoic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 3-biphenyl-4-yl-acrylic acid methyl ester (9.384 g, 39.38 mmol) in THF (120 ml) and MeOH (80 ml) was added 1N KOH (79 ml) and the mixture refluxed. After 3 h, heating was stopped. The reaction mixture was concentrated to about 50 ml, diluted with water (200 ml) and acidified with 2N HCl (80 ml). EtOAc (1000 ml) was added and the whole mixture heated to boiling to dissolve all solids. After cooling, the layers were separated and the organic layer washed with 1N HCl (2×70 ml), water (3×70 ml), brine (2×50 ml), dried over Na2SO4, filtered, concentrated and dried to give 3-biphenyl-4-yl-acrylic acid (7.393 g, 32.966 mmol, 84%) as a white solid, dec. 223-226° C. 1H NMR (DMSO-d6) δ 6.58 (d, 1H), 7.37-7.53 (m, 3H), 7.62 (d, 1H), 7.70-7.84 (m, 6H), 12.40 (s, 1H); mass spectrum [ES(−)], m/z 223 (M−H)−.

Aufarbeitung

  1. temperaturethe mixture refluxed
  2. temperatureheating
  3. concentrationThe reaction mixture was concentrated to about 50 ml
  4. additiondiluted with water (200 ml)
  5. additionEtOAc (1000 ml) was added
  6. temperaturethe whole mixture heated
  7. dissolutionto dissolve all solids
  8. temperatureAfter cooling
  9. customthe layers were separated
  10. washthe organic layer washed with 1N HCl (2×70 ml), water (3×70 ml), brine (2×50 ml)
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8a6ec0d1cadf4067844245e9ccae4d46
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420083B2

Verknüpfte Notizen

Wird geladen…