Bromocyclopentane → HCID 6484666, Verbindung

HRID 378969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 378969
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C.O>[CH:18]1([O:1][C:2]2[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

6

Edukt 3

HCID 8728BromocyclopentaneHCID 8991o-VanillinHCID 11430Potassium Carbonate

Produkt 1

HCID 6484666HCID 6484666, VerbindungAusbeute 615 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-3-methoxy-benzaldehyde (10 g, 6.57 mmoles), K2CO3 (18.16 g, 131 mmoles), cyclopentyl-bromide (14.05 ml, 131 mmoles) in absolute ethanol (150 ml) under nitrogen was refluxed under stirring for 55 hours. The mixture was diluted with water, thrice extracted in ethyl acetate, washed with water, anhydrified over Na2SO4 and evaporated to dryness, the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5) to give 8.9 g of the title product (yield: 61%).

Aufarbeitung

  1. temperaturewas refluxed
  2. extractionextracted in ethyl acetate
  3. washwashed with water
  4. customevaporated to dryness
  5. customthe yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-114a80d13eb54f2fb9c1fec91ebb6b9f
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297257B1

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