N,N-Dimethylaniline → 3-Allyl-biphenyl-4-ol

HRID 970822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970822
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)C=C.CN(C)[C:19]1[CH:24]=CC=C[CH:20]=1>C(OCC)C>[CH2:24]([C:10]1[CH:9]=[C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][C:5]=1[OH:4])[CH:19]=[CH2:20]

Komponenten

4

Edukt 2

HCID 949N,N-DimethylanilineHCID 2579864-Allyloxybiphenyl

Produkt 1

HCID 2584593-Allyl-biphenyl-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 4-allyloxy-biphenyl 65 (5.03 g, 23.9 mmol) in 20 ml of dimethylaniline was heated at 170° C. for 5 hr. The mixture was diluted with 250 ml diethyl ether and washed with 1M HCl solution. The ether phase was washed with brine, dried and concentrated to give a brown solid. The crude product was recrystallized from cyclohexane to give 2.69 g 3-allyl-biphenyl-4-ol 66. The mother liquor was concentrated and chromatographed (7% ethyl acetate/hexane) to give an additional 2.13 g of 2-allyl-4-phenyl-phenol 66.

Aufarbeitung

  1. washwashed with 1M HCl solution
  2. washThe ether phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a brown solid
  6. customThe crude product was recrystallized from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-4f20fa4c84d641a382fad03a12e6dd22
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312230B2

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