Phenol → Phenyl 2,4-dihydroxybenzoate

HRID 962858

Reaktionsgleichung

Reaktionsgleichung von HRID 962858
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1.S(Cl)(Cl)=O>CN(C)C=O>[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5]

Komponenten

6

Edukt 4

HCID 996PhenolHCID 1140TolueneHCID 14912,4-Dihydroxybenzoic AcidHCID 24386Thionyl Chloride

Produkt 1

HCID 14523517Phenyl 2,4-dihydroxybenzoateAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 1.5 l sulfonating flask equipped with stirrer, condenser, dropping funnel and gas outlet is charged with 154.1 g (1.0 mol) of 2,4-dihydroxybenzoic acid, 141.2 g (1.5 mol) of phenol, 500 ml of toluene and 1 ml of dimethylformamide. 178.5 g (1.5 mol) of thionyl chloride are then added dropwise at an internal temperature of 100°-105° C. over a period of 2.5 hours. The reddish clear solution is then refluxed overnight (110°-115° C.). The toluene and the phenol are distilled off in vacuo, the highly viscous residue (271.5 g) is stirred in 300 ml of 7:3 toluene/cyclohexane, and the product is allowed to crystallize overnight. The precipitate is filtered off with suction while cold (10° C.) and washed with 3×50 ml of 7:3 toluene/cyclohexane. It is dried at 80° C. in vacuo to give 125.5 g (54.4% of theory) of phenyl 2,4-dihydroxybenzoate (m.p. 135°-137° C.).

Aufarbeitung

  1. customequipped with stirrer, condenser
  2. temperatureThe reddish clear solution is then refluxed overnight (110°-115° C.)
  3. distillationThe toluene and the phenol are distilled off in vacuo
  4. customto crystallize overnight
  5. filtrationThe precipitate is filtered off with suction while cold (10° C.)
  6. washwashed with 3×50 ml of 7:3 toluene/cyclohexane
  7. customIt is dried at 80° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4cb62abb77434e16bc0f7f29dbd5b79d
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760111

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