Lithium iodide → 2,6-Dichloro-4-(hydroxymethyl)benzoic acid

HRID 875413

Reaktionsgleichung

Reaktionsgleichung von HRID 875413
[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[C:8]([Cl:14])[C:3]=1[C:4]([O:6]C)=[O:5].[I-].[Li+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[C:8]([Cl:14])[C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

4

Edukt 2

HCID 66321Lithium iodideHCID 66712920Methyl 2,6-dichloro-4-(hydroxymethyl)benzoate

Produkt 1

HCID 667205832,6-Dichloro-4-(hydroxymethyl)benzoic acidAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A suspension of methyl 2,6-dichloro-4-(hydroxymethyl)benzoate (5.3 g, 22 mmol) in pyridine (20 mL) was treated with anhydrous lithium iodide (9 g, 67 mmol). The resulting reaction mixture was heated to reflux for 5 hours, cooled to room temperature and concentrated under vacuum. The residue was diluted with water and acidified with dilute hydrochloric acid (pH 2-3) and partitioned with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, concentrated and the residue obtained upon triturating with diethyl ether afforded 2,6-dichloro-4-(hydroxymethyl)benzoic acid as a pale yellow solid (3.5 g, 70%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 5 hours
  4. concentrationconcentrated under vacuum
  5. additionThe residue was diluted with water
  6. custompartitioned with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customthe residue obtained
  11. customupon triturating with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d82c72fb81b846f0b43003ab6ef27537
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980911B2

Verknüpfte Notizen

Wird geladen…