[asa029]

Hi,

I'm going to prepare some simple, asymmetric ethers for further synthesis and I'm looking into the simplest, easiest methods. The general type of ethers I'm interested in would proparagyl ether with an aliphatic part like ethyl proparagyl ether or more bulky diphenylmethyl proparagyl ether.

I'm thinking of using an acidic resin/co-polymer like a Dowex, proparagyl alcohol and for example ethanol as substrate, reflux for some hours and distillation as work-up.

Any input or suggestions for better methods?

[asa029]

PS: Im aware that the method would yield homoethers as well (like diproparagyl ether and diethyl ether), but the yield isn't crucial as long as the side-products are readily removed by destillation.

[Honclbrif]

http://en.wikipedia.org/wiki/Williamson_ether_synthesis

More substituted side = alkoxide, less substituted side = leaving group.