Hydrochloric Acid → 5-Hexene-1,2,3-triol
Reaktionsgleichung
CC1(C)[O:6][CH:5]([CH:7]([CH2:9][CH:10]=[CH2:11])[OH:8])[CH2:4][O:3]1.Cl.C(Cl)(Cl)Cl>O1CCCC1>[CH2:4]([OH:3])[CH:5]([OH:6])[CH:7]([OH:8])[CH2:9][CH:10]=[CH2:11]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 11 g of [R-(R*,R*)]-2,2-dimethyl-alpha-2-propenyl-1,3-dioxolane-4-methanol, prepared by the procedure described in J.. Am. Chem. Soc., 1985, 107(26), 8186-8190, in 300 ml of 1:1 tetrahydrofuran: 2N hydrochloric acid is heated at the reflux temperature of the solvents for 2 hours. Chloroform is added and the layers are separated. The aqueous layer is re-extracted 2X with chloroform. The aqueous layer is neutralized with potassium carbonate and exhaustively extracted with 80% chloroform/iso-propanol. The combined organic layers are concentrated in vacuo to give 7.51 g of the desired product.