http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3808232-A

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http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D311-92
filingDate 1972-07-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1974-04-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_1543fa382a21fdbe6c700bc91cbbdf1b
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_45787d0dd9e1e618a68cde5995459859
publicationDate 1974-04-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-3808232-A
titleOfInvention Process of preparing 4-halomethyl coumarins and compounds
abstract A PROCESS FOR THE PREPARATION OF 4-HALOMETHYL-5-R1 SUBSTITUTED-6-R2 SUBSTUTUTED-7-R3 SUBSTITUTED-8-R4 SUBSTITUTEDCOUMARIN HAVING THE GENERAL FORMULA: 4-(X-CH2-),5-R1,6-R2,7-R3,8-R4-2H-CHROMEN-2-ONE WHEREIN X IS CHLORINE OR BROMINE, R1 IS -H OR -CH3, R2 IS -H, AN ALKYL GROUP HAVING 1 TO 4 CARBON ATOMS, -OH,-OCH3 OR A HALOGEN ATOM, R3 IS -H, AN ALKYL GROUP HAVING 1 TO 4 CARBON ATOMS, -OH, -OCH3 OR A HALOGEN ATOMS, AND R4 IS -H OR -CH3, OR WHEREIN WHEN R1 AND R2 ARE -H OR -CH3, R3 AND R4 CAN FORM A BENZO GROUP, OR WHEREIN R1 AND R2 CAN FORM A BENZO GROUP WHEN R3 AND R4 ARE -H OR -CH3 IS DISCLOSED. THE PROCESS INVOLVES REACTING DIKETENE WITH HALOGEN AT TEMPERATURES BETWEEN -30* AND -10*C. IN A SOLVENT. THE SOLVENT IS INERT TO HALOGEN AND IS NOT MISCIBLE WITH SULFURIC ACID. Y-HALOACETOACETIC HALIDE IS FORMED. THE Y-HALOACETOACETIC HALIDE IS IMMEDIATELY CONVERTED USING A PHENOL TO A CORRESPONDING PHENYL ESTER. THE CORRESPONDING PHENYL ESTER, WITHOUT SEPARATING THE SOLVENT, IS TREATED AT A TEMPERATURE BETWEEN -30* TO + 30*C. WITH CONCENTRATED SULFURIC ACID. TWO PHASES FORM. THE LOWER SULFURIC ACID LAYER IS SEPARATED AND IS HYDROLLIZED WITH AN ICE WATER ADMIXTURE, 4-HALOMETHYL-5-R1 SUBSTITUTED-6-R2 SUBSTITUTED7-R3 SUBSTITUTED-8-R4 SUBSTITUTED COUMARIN RECIPITATES. 4-HALOMETHYL-5-R1 SUBSTITUTED -6-R2 SUBSTITUTED-7-R3 SUBSTITUTED-8-R44 SUBSTITUTED-COUMARIN IS THEN ISOLATED. CERTAIN NEW SUBSTITUTED 4-GALOMETHYL-COUMARINS ARE ALSO DISCLOSED.
isCitedBy http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3891569-A
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priorityDate 1971-09-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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