The reaction given in Fig. P18.82, used to prepare the drug mephenesin (a skeletal muscle relaxant), appears to be a simple Williamson ether synthesis. During this reaction, a precipitate of NaCl forms after only about 10 minutes, but a considerably longer reaction time is required to obtain a good yield of mephenesin. Taking these facts into account, suggest a mechanism for this reaction.

Transcribed Image Text:

CH3 OH T -O- Na+ + Cl-CH₂CHCH₂OH Figure P18.82 2h ethanol-water CH3 OH -O-CH₂CHCH₂OH + NaCl- mephenesin