Chloroacetic Acid → Benzoic acid, 2-(carboxymethoxy)-

HRID 1362364

Reaktionsgleichung

Reaktionsgleichung von HRID 1362364
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[Na+].Cl[CH2:14][C:15]([OH:17])=[O:16]>O>[C:15]([CH2:14][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])([OH:17])=[O:16]

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 338Salicylic AcidHCID 14798Sodium Hydroxide

Produkt 1

HCID 69461Benzoic acid, 2-(carboxymethoxy)-Ausbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of salicylic acid (20 g, 145 mmol) in water (200 mL) is added carefully sodium hydroxide (60 g, 1.45 mol) followed by chloroacetic acid (27 g, 290 mmol). The mixture is refluxed for 5 d, cooled to room temperature and the precipitate is filtered and dried. Trituration with hexanes yielded the title compound (6.84 g, 24%) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ 7.65-7.66 (dd, 1H, J=8.0, 2.0 Hz), 7.45-7.47 (dd, 1H, J=8.0, 2.0 Hz), 6.97-7.05 (m, 2H), 4.77 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture is refluxed for 5 d
  2. filtrationthe precipitate is filtered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cb4210f1881b46afa449d7d980a42260
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

Verknüpfte Notizen

Wird geladen…