Water → 3-Chloro-o-cresol

HRID 354258

Reaktionsgleichung

Reaktionsgleichung von HRID 354258
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[CH3:9].[OH-].[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)[O:14]C1.O>C(O)COCCO>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:14])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 83682,6-DichlorotolueneHCID 14797Potassium HydroxideHCID 26541Dibenzo-18-crown-6

Produkt 1

HCID 148563-Chloro-o-cresol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8117Diethylene GlycolLösungsmittel

Versuchsvorschrift

16.1 g (0.1 mol) of 2,6-dichlorotoluene, 19.8 g (0.3 mol) of potassium hydroxide (85%) and 0.3 g of dibenzo-18-crown-6 are heated in 30 ml of diethylene glycol at a bath temperature of 190° C. with reflux for 16 hours. The water released during the reaction is distilled off. After cooling, the reaction mixture is stirred with 100 ml of water until a solution is obtained and extracted three times with 50 ml of dichloromethane. The aqueous phase is admixed with 35 ml of 30% hydrochloric acid and extracted three times with 70 ml of dichloromethane. The organic phases are dried and concentrated under reduced pressure. 3-Chloro-2-methylphenol is obtained as a solid (11.5 g, content by HPLC: 97%, 78% of theory).

Aufarbeitung

  1. temperaturewith reflux for 16 hours
  2. distillationis distilled off
  3. temperatureAfter cooling
  4. customis obtained
  5. extractionextracted three times with 50 ml of dichloromethane
  6. extractionextracted three times with 70 ml of dichloromethane
  7. customThe organic phases are dried
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-47cdf0d64c614343b118c960586e4a29
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756512B2

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