1-Adamantanol → 3-(1-Admantyl)-4'-iodobiphenyl-4-ol

HRID 710463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710463
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]12(O)[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2>CC(O)=O.CCOC(C)=O>[C:15]12([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=4)[CH:13]=[CH:12][C:11]=3[OH:14])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2

Komponenten

5

Edukt 2

HCID 641521-AdamantanolHCID 20640304-Hydroxy-4'-iodobiphenyl

Produkt 1

HCID 871266403-(1-Admantyl)-4'-iodobiphenyl-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 4′-iodobiphenyl-4-ol (0.332 g, 2 mmol) and 1-admantanol (0.15 g, 0.51 mmol) in AcOH (2 ml) concentrated H2SO4 (0.5 ml) was added and the reaction mixture was stirred for 50 h at room temperature. This was diluted to 100 ml with EtOAc and washed with NaHCO3 solution, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was crystallized from MeOH to give the product (0.195 g; 93%), as a colourless paste. 1H NMR (CDCl3) 1.78 (m, 6H); 2.07 (s, 3H); 2.15 (s, 6H); 6.69 (d, 1H, J=8.15 Hz); 7.21-7.28 (m, 3H); 7.37 (d, 1H, J=2.28 Hz); 7.69 (d, 2H, J=8.45 Hz).

Aufarbeitung

  1. additionwas added
  2. washwashed with NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was crystallized from MeOH
  7. customto give the product (0.195 g; 93%)

Quellen und Nachweise

ORD-Eintrag
ord-a7276908eb5d46acb1f31a4b8b789464
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

Notizen zur Reaktion

Wird geladen…