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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1721537Erstellt: 26. Oktober 2026

Hydrochloric Acid → 1,1'-Binaphthalene, 2,2'-dimethyl-

https://huagongshe.com/reaction/1721537

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktHydrochloric AcidHCID 313—
EduktPhosphineHCID 24404—
Edukt1-Bromo-2-methylnaphthaleneHCID 75754—
Edukt1,4-Bis(diphenylphosphino)butaneHCID 82124—
Edukt2,2'-Bis(diphenylphosphinomethoxy)-1,1'-binaphthylHCID 11828568—
EduktHCID 178422613HCID 178422613—
Katalysatorpalladium(II) acetateHCID 167845—
LösungsmittelWaterHCID 962—
LösungsmittelTolueneHCID 1140—
Produkt1,1'-Binaphthalene, 2,2'-dimethyl-HCID 141748—

Reaktionsbedingungen

Temperatur80 °C

Reaktionsschritte

2-Methyl-1-naphthylmagnesium bromide prepared according to Example 1 in toluene is added in the absence of air and moisture to a suspension, heated to 70° to 80° C., of 31.0 g (0.14 mol) of 1-bromo-2-methylnaphthalene, 0.0014 mol of the phosphine of the formula (I) 1,4-bis(diphenylphosphino)butane; 2,2'-bis(diphenylphosphinomethoxy)-1,1'-binaphthyl! or 0.0028 mol of the phosphine of the formula (II) (triphenylphosphine) and 0.31 g (0.0014 mol) of palladium(II) acetate in 50 ml of toluene. The mixture is then heated at 80° C. for another hour, cooled to 25° C., and 100 ml of water and 50 ml of 2N hydrochloric acid are added in succession to the reaction mixture. The phases are separated, the aqueous phase is extracted with 50 ml of toluene, and the combined organic phases are concentrated in vacuo. Distillation of the oily, brown residue in a high vacuum gives a pale yellow oil having a boiling point of 175° to 180° C./0.1 to 0.2 mbar. The yields can be found in Table 1 below.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05510554
Quelldatensatzuspto-grants-1996_04
ORD IDord-4366f3247c8f4e719e3b89237ebb09a7
Quellennotizuspto-grants-1996_04