1,4,7,10-tetraoxacyclododec-2-ylmethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction in pyridine (13 ml) of 1,4,7,10-tetraoxacyclo-dodecane-2-methanol (5 g) with p-toluenesulphonyl chloride (5 g) produces 1,4,7,10-tetraoxacyclododecane-2-methanol p-toluenesulphonate (8 g; m.p. 49°-51° C. from diethyl ether). Subsequent reaction with diethyl malonate (3.36 ml) and potassium tert-butoxide (3.47 g) in N-methyl pyrrolidone (30 ml) yields [(1,4,7,10-tetraoxacyclododecane-2-yl)methyl]-malonate diethyl ester as a viscous oil that is treated with aqueous lithium hydroxide 0.8 g) to obtain pure [(1,4,7,10-tetraoxacyclododecane-2-yl)methyl]-malonic acid N.M.R. (CDCl3): 2.08-2.19; 3.48-3.82; 9.38].

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction in pyridine (13 ml) of 1,4,7,10-tetraoxacyclo-dodecane-2-methanol (5 g) with p-toluenesulphonyl chloride (5 g) produces 1,4,7,10-tetraoxacyclododecane-2-methanol p-toluenesulphonate (8 g; m.p. 49°-51° C. from diethyl ether). Subsequent reaction with diethyl malonate (3.36 ml) and potassium tert-butoxide (3.47 g) in N-methyl pyrrolidone (30 ml) yields [(1,4,7,10-tetraoxacyclododecane-2-yl)methyl]-malonate diethyl ester as a viscous oil that is treated with aqueous lithium hydroxide 0.8 g) to obtain pure [(1,4,7,10-tetraoxacyclododecane-2-yl)methyl]-malonic acid N.M.R. (CDCl3): 2.08-2.19; 3.48-3.82; 9.38].