http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0271307-B1

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filingDate 1987-12-08-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1992-01-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1992-01-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-0271307-B1
titleOfInvention Method for producing alkenylthiophenols and their esters
abstract 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 O-(acylaryl) N,N-di(organo)thiocarbamate, e.g., O-(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.
priorityDate 1986-12-10-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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