http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1369646-A

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http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D307-68
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http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D307-68
filingDate 1971-10-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1974-10-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1369646-A
titleOfInvention Preparation of 3-furoate esters
abstract 1369646 Bisulphite addition products; 3- furoate esters CPC INTERNATIONAL Inc 12 Oct 1971 [22 Oct 1970] 47533/71 Heading C2C Bisulphite addition products are obtained by reacting a 4-(C 1-6 alkylene) ketal-2-formyl valeric acid ester with an aqueous solution of alkali metal bisulphite (e.g. NaHSO 3 ). The reaction is generally effected at ambient temperature (e.g. 20-50‹ C.). Preferred starting materials are C 1-6 alkyl esters and those valeric acid esters which contain an aryl group on the 5-carbon atom. 3-Furoate esters are obtained from these bisulphite addition products by cyclization using a strong mineral acid (e.g. H 2 SO 4 at 20-50‹ C.). The bisulphite addition product is preferably washed with toluene prior to the cyclization. The reactions are illustrated in the following pair of equations in which R is alkyl or phenyl: The examples describe the conversion of ethyl 2-formyl-4-ethylenedioxy-5-phenyl valerate to its sodium bisulphite addition product-sodium 1 - hydroxy - 2 - carbethoxy - 4 - ethylenedioxy- 5-phenyl pentane sulphonate-and the reaction of the latter with 90% H 2 SO 4 to form ethyl 5- benzyl-3-furoate. The 2-formyl starting material is itself obtained from ethyl 4-ethylenedioxy-5- phenyl valerate by reaction with NaOEt/ HCO 2 Et and acidification of the 2-sodiohydroxy-methylene intermediate.
priorityDate 1970-10-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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