Acetic Acid → 4'-Methoxy-4-(2-methylbutyl)biphenyl

HRID 231007

Reaktionsgleichung

Reaktionsgleichung von HRID 231007
Cl.C(O)(=O)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=O)[CH:21]([CH3:24])[CH2:22][CH3:23])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>[Zn].[Hg]Cl.CCOCC.O.C1(C)C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([CH3:24])[CH2:22][CH3:23])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Komponenten

9

Edukt 3

HCID 176Acetic AcidHCID 313Hydrochloric Acid3×HCID 151139424'-Methoxy-4-(2-methylbutyryl)biphenyl

Produkt 1

HCID 117369194'-Methoxy-4-(2-methylbutyl)biphenylAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23994ZincKatalysatorHCID 24182Mercurous ChlorideKatalysatorHCID 962WaterLösungsmittel3×HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

13.6 g of zinc powder, 1.4 g of mercury chloride, 0.7 ml of conc. hydrochloric acid, and 20 ml of water were mixed with shaking for five minutes, and then the supernatant solution was flowed out. To the obtained zinc amalgam, 10 ml of water, 24 ml of conc. hydrochloric acid, 1 ml of acetic acid, 14 ml of toluene, and 38 m moles(10.2 g) of 4'-methoxy-4-(2-methylbutyryl)biphenyl were added, and then refluxed for 20 hours. In the mean time, 5 ml portions of conc. hydrochloric acid was successively added every five hours. The reaction solution was cooled to room temperature, then, after the addition of water, ether extracted. The extract was washed with water, dried, and concentrated, and then purified by column chromatography, to obtain 7.1 g of 4'-methoxy-4-(2-methylbutyl)biphenyl. (yield: 74%)

Aufarbeitung

  1. temperaturerefluxed for 20 hours
  2. extractionextracted
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-691cfbe060bf459d9b6850de7d6a6d4e
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04844835

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