Reaktion #51281

Reaktionsgleichung

resorcinol

bromoadmantane

resorcinol

→

product

Ausbeute 66.8%

4,6-bis(adamantyl)resorcinol

Ausbeute 66.8%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 250-mL 3-neck flask, equipped with nitrogen inlet
2. 2
   SonstigeThe solvent was removed
3. 3
   Sonstigethe solid was crystallized from hexanes (150 mL)
4. 4
   SonstigeThe disubstituted product was obtained in 66.8% yield (25.26 g) as a white solid

Vorschrift

Into a 250-mL 3-neck flask, equipped with nitrogen inlet, thermocouple and condenser, were added resorcinol (11.00 g, 100.0 mMol), bromoadmantane (44.02 g, 205.1 mMol) and toluene (150 mL). The mixture was heated to 110° C. and became a clear solution. The reaction was allowed to continue for 48 h, at which time TLC showed that all the resorcinol had disappeared. The solvent was removed and the solid was crystallized from hexanes (150 mL). The disubstituted product was obtained in 66.8% yield (25.26 g) as a white solid. Another 5.10 g product was obtained by silica gel column chromatography of the concentrated mother liquor after the first crop. The total yield of the product was 80.3%. Characterization of the product was by proton NMR, HPLC, FTIR and MS.

Quelle