Hydrochloric Acid → 2-(3,4-dichlorophenyl)pent-4-enoic Acid

HRID 2402138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2402138
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([O:12]C)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 11807390Methyl 2-(3,4-dichlorophenyl)pent-4-enoate

Produkt 1

HCID 110102122-(3,4-dichlorophenyl)pent-4-enoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(3,4-dichlorophenyl)pent-4-enoate (2.47 g, 9.53 mmol) in tetrahydrofuran (15.0 mL) was added a solution of lithium hydroxide monohydrate (2.00 g, 47.6 mmol) in water (15.0 mL). The mixture was vigorously stirred at rt for 12 hrs. The resulting mixture was acidified by addition of 12.0 M of hydrochloric acid in water (3.97 mL, 47.6 mmol) at 0° C., and extracted with EtOAc (×3). The combined organic layer was dried and concentrated to provide 2-(3,4-dichlorophenyl)pent-4-enoic acid as a yellow syrup (2.65 g, quantitative). 1H NMR (400 MHz, CDCl3) δ 7.45-7.35 (m, 2H), 7.21-7.11 (dd, J=8.3, 2.1 Hz, 1H), 5.76-5.59 (ddt, J=17.0, 10.2, 6.8 Hz, 1H), 5.14-4.99 (m, 2H), 3.65-3.56 (t, J=7.7 Hz, 1H), 2.88-2.74 (dt, J=14.8, 7.5 Hz, 1H), 2.58-2.43 (dt, J=14.3, 6.9 Hz, 1H).

Aufarbeitung

  1. extractionextracted with EtOAc (×3)
  2. customThe combined organic layer was dried
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-21463f6bcf384e3087618e7595befca1
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796271B2

Notizen zur Reaktion

Wird geladen…