Lithium hydroxide, monohydrate → 4-(2,4-Dichlorophenoxy)butyric acid

HRID 1875311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875311
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]CC)=[O:9].O[Li].O>C1COCC1.O>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 12375252Ethyl 4-(2,4-dichloro-phenoxy)butanoate

Produkt 1

HCID 14894-(2,4-Dichlorophenoxy)butyric acidAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(2,4-dichlorophenoxy)-butyrate (57 g, crude from last step, about 0.2 mol) in THF (500 mL) and water (500 mL) was added LiOH.H2O (12.6 g, 0.3 mol), and the reaction mixture was stirred for 5 h at RT. The mixture was washed with Et2O (3×200 mL), and the aqueous layer was acidified by addition of HCl (20%) to pH ˜2. The mixture was extracted with EtOAc (3×400 mL), the combined organic extracts were washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give the butyric acid (37 g, 74.3% from 2,4-dichlorophenol) as a white solid. 1H-NMR (CDCl3): δ 7.36 (d, 1H, J=8.8 Hz), 7.18 (dd, 1H, J1=8.8 Hz, J2=2.4 Hz), 6.84 (d, 1H, J=8.8 Hz), 4.07 t, 2H, J=7.2 Hz), 2.64 (t, 2H, J=7.2 Hz), 2.17 (p, 2H, J=6.4 Hz).

Aufarbeitung

  1. washThe mixture was washed with Et2O (3×200 mL)
  2. additionthe aqueous layer was acidified by addition of HCl (20%) to pH ˜2
  3. extractionThe mixture was extracted with EtOAc (3×400 mL)
  4. washthe combined organic extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-269b1d1323624eddb28e1e0f5f407973
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309543B2

Notizen zur Reaktion

Wird geladen…