Acetone → 1-[4-(3-Chloropropoxy)-2-hydroxy-5-methoxyphenyl]ethanone

HRID 264240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 264240
[CH3:1][C:2]([C:4]1[C:9]([OH:10])=[CH:8][C:7]([OH:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[Cl:20][CH2:21][CH2:22][CH2:23]Br.CC(C)=O>O>[Cl:20][CH2:21][CH2:22][CH2:23][O:11][C:7]1[C:6]([O:12][CH3:13])=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[C:9]([OH:10])[CH:8]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 498505401-(2,4-Dihydroxy-5-methoxyphenyl)ethan-1-one

Produkt 1

HCID 184672431-[4-(3-Chloropropoxy)-2-hydroxy-5-methoxyphenyl]ethanoneAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2,4-dihydroxy-5-methoxyacetophenone (1.4 g, 7.7 mmol), K2CO3 (1.4 g, 10.0 mmol), 3-chlorobromopropane (1.6 g, 10.0 mmol) and acetone (25 mL) was stirred and refluxed under N2 for 16 hours. The reaction was poured into H2O, and the aqueous suspension was extracted with ethyl acetate. The extract was washed (H2O, brine) dried (MgSO4) and concentrated to yield 1.4 g of an off-white solid. Recrystallization twice from ethanol afforded 0.4 g of the alkylated phenol as a solid, m.p. 99°-101° C.

Aufarbeitung

  1. temperaturerefluxed under N2 for 16 hours
  2. extractionthe aqueous suspension was extracted with ethyl acetate
  3. washThe extract was washed (H2O, brine)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f2844f5f6df643e18a516adb5648bd40
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646161

Notizen zur Reaktion

Wird geladen…