Method for producing alkenylthiophenols and their esters

Details Method for producing alkenylthiophenols and their esters Method for producing alkenylthiophenols and their esters

C - Chemistry, Metallurgy

07

C

260/471.2, 260/6

C07C 321/26 (2006.01) C07C 45/46 (2006.01) C07C 45/54 (2006.01) C07C 327/26 (2006.01)

Patent

CA 1274535

ABSTRACT OF THE DISCLOSURE A method is provided for preparing alkenylthiophenols, e.g., para-vinylthiophenol, or their esters, e.g., para-vinylthiophenol acetate by reacting a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone (4-HAP) with an N,N-di(organo)thiocarbamoyl halide, e.g., N,N-dimethylthiocarbamoyl chloride (DMTC) to form an 0-(acylaryl) N,N-di(organo)thiocarbamate, e.g., 0-(4'-acetophenyl) N,N-dimethylthiocarbamate, and pyrolytically rearranging the latter compound to form an S-(acylaryl) N,N-di(organo)thiocarbamate, e.g., S-(4'-acetophenyl) N,N-dimethylthiocarbamate. In one procedure, the latter compound is directly reduced to form an S-(1-hydroxyalkylaryl) N,N-di(organo) thiocarbamate, e.g., S-[4'-(1-hydroxyethyl)phenyl] N,N-dimethylthiocarbamate, which is either hydrolyzed to form a (1-hydroxyalkyl) thiophenol, e.g., 4'-(1-hydroxyethyl) thiophenol, which, optionally after acylation of its thiol group, is dehydrated to form the alkenylthiophenol wherein the double bond is at the ring-bonded carbon atom, e.g., para-vinylthiophenol, or the S-(1-hydroxyalkylaryl) N,N-di(organo) thiocarbamate is dehydrated to form an S-(alkenylaryl) N,N-di(organo) thiocarbamate, e.g., S-(4-vinylphenyl) N,N-dimethylthiocarbamate which is hydrolyzed to form the alkenylthiophenol. In an alternative procedure, the S-(acylaryl) N,N-di(organo)thiocarbamate is hydrolyzed and the resulting thiol acylated with an acylating agent, e.g., acetyl chloride, to produce an acylthiophenol ester, e.g., 4-acetothiophenol acetate, which is then reduced and hydrolyzed to produce the (1-hydroxyalkyl) thiophenol. The latter compound is then dehydrated to produce the alkenylthiophenol, or acylated and dehydrated to produce the alkenylthiophenol thioester, as described in the first procedure.

553328

Affiliated with

Also associated with

Rating

Method for producing alkenylthiophenols and their esters does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for producing alkenylthiophenols and their esters, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for producing alkenylthiophenols and their esters will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFCA-PAI-O-1174559