Carbonic acid, 1-chloroethyl ethyl ester → HCID 178473648, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trans-4-(tert.-butoxycarbonylaminomethyl) cyclohexanecarboxylic acid (25.7 g; 0.1 mol) and tetrabutylammonium hydrogen sulfate (34 g; 0.1 mol) in 2N sodium hydroxide (100 ml) was extracted with ethanolfree chloroform. The chloroform solution was dried and evaporated to give 50 g. This was dissolved in trichloroethylene (200 ml) and ethyl (1-chloroethyl) carbonate (16.8 g; 0.11 mol) was added. After refluxing for 3 h the solution was washed with dilute sulphuric acid, sodium bicarbonate solution and water. After evaporation of chloroform the residue was dissolved in ethyl acetate cooled to 0° C. To this solution a cold solution of hydrochloric acid in ethyl acetate was added. After 3 h at ice bath temperature the solvent was evaporated to give 23 g. This was dissolved in isopropyl alcohol and precipitated with diisopropyl ether. Yield 15 g (49%), m.p. 139° C.

Provenance & Evidence