Phenol → Benzenemethanol, 3-phenoxy-, 1-acetate

HRID 247723

Reaktionsgleichung

Reaktionsgleichung von HRID 247723
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C1(C)C(C)=CC=CC=1.[C:18]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25](Cl)[CH:24]=1)(=[O:20])[CH3:19]>C1(C)C=CC=CC=1>[C:18]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:24]=1)(=[O:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 996PhenolHCID 7237O-XyleneHCID 14797Potassium HydroxideHCID 11217649(3-chlorophenyl)methyl Acetate

Produkt 1

HCID 170904Benzenemethanol, 3-phenoxy-, 1-acetateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

18.07 g. (0.192 mole) of phenol, 8.42 g. (0.15 mole) of potassium hydroxide and 20 cm3 of xylene are weighed together. The water is azeotropically distilled with stirring and boiling then the xylene is also distilled. To the reaction mixture 1.0 g. of copper(I) chloride and 1.0 g. of activated copper are added and in oil bath of 160° C. 18.07 g. (0.1 mole) of 3-chlorobenzyl acetate are dropped during 70 minutes then stirred at the same temperature for four hours. After cooling 25 cm3. of toluene are added to the reaction mixture, then the reaction mixture is filtered off and washed with 25 cm3. of toluene. The filtrate is washed with a mixture of 30 cm3. 15% sodium chloride solution and 2 cm3. 40% sodium hydroxide solution. The organic phase is evaporated and the residue is distilled in vacuo. 17.68 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 138°-144° C./40 Pa, nD20 : 1.562, yield 73%.

Aufarbeitung

  1. distillationThe water is azeotropically distilled
  2. distillationthe xylene is also distilled
  3. additionof activated copper are added and in oil bath of 160° C
  4. stirringthen stirred at the same temperature for four hours
  5. temperatureAfter cooling 25 cm3
  6. filtrationthe reaction mixture is filtered off
  7. washwashed with 25 cm3
  8. washThe filtrate is washed with a mixture of 30 cm3
  9. customThe organic phase is evaporated
  10. distillationthe residue is distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e8c412d68db949cc810e5b2ed41843a1
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04709081

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