Water → cis-4-Cyanomethyl-5-benzyloxymethylcyclohex-1-ene

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Cyanide	HCID 9032	—
Reactant	cis-4-p-Toluene-sulphonyloxymethyl-5-benzyloxymethyl cyclohex-1-ene	HCID 86740865	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	cis-4-Cyanomethyl-5-benzyloxymethylcyclohex-1-ene	HCID 67914518	86.8%

Reaction Conditions

Temperature	100 °C

Reaction Steps

The p-toluene sulphonyl ester/benzyl ether (3) (12 g) in dimethylsulphoxide (DMSO) (15 ml) is added with stirring to potassium cyanide (3 g) in DMSO (20 ml). The mixture is heated at 100° C. under nitrogen for 6 hours and is then cooled, poured into water and the product extracted with ether. The solvent is removed and the residue purified on a Florisil column, eluting with petroleum ether-benzene (1:1) to give the title compound as an oil (6.5 g, ca. 80%) νmax (film) 2220 and 1600 cm-1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05028733
Source dataset	uspto-grants-1991_07
ORD ID	ord-e719d2e966e342c890694f6e6c909969
Source note	uspto-grants-1991_07