Potassium Hydroxide → 3-(o-Hydroxymethylphenylthio)-4-hydroxybenzoic acid

HRID 2418496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2418496
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].I[C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[OH:20])[C:14]([OH:16])=[O:15].[OH-].[K+]>O.[Cu]>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[S:1][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[OH:20])[C:14]([OH:16])=[O:15]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 1382782-MercaptobenzenemethanolHCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)

Produkt 1

HCID 202039813-(o-Hydroxymethylphenylthio)-4-hydroxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 25 g o-mercaptobenzyl alcohol (0.18 mole), 39.6 g 3-iodo-4-hydroxy benzoic acid (0.15 mole), 11.43 g copper powder (0.18 mole), 70 ml 40% aqueous potassium hydroxide solution (0.5 mole) and 300 ml water was placed under nitrogen atmosphere and stirred under reflux for 18 hours. After cooling the mixture was diluted with 400 ml of water and extracted twice with 100 ml of ethyl acetate to remove neutral products. The aqueous fraction was filtered and the filtrate acidified with conc. HCl to afford the title compound as an oil which solidified and was filtered. There was obtained 32.8 g solid.

Aufarbeitung

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling the mixture
  3. extractionextracted twice with 100 ml of ethyl acetate
  4. customto remove neutral products
  5. filtrationThe aqueous fraction was filtered

Quellen und Nachweise

ORD-Eintrag
ord-1deed9c350d74db3a5f0cd7fe6a2e4b0
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04472586

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