1952
DOI: 10.1039/jr9520003634
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696. The hydroxynaphthoate series. Part I. A synthesis of 4-hydroxynaphthoic acid and its simple esters

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Cited by 3 publications
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“…In the molecule of 4-(benzyloxy)-1-bromonaphtalene ( 3 ), the bromine atom was first replaced by nitrile functional group in Rosenmund – von Braun reaction [ [21] , [22] ]. By the reduction of formed nitrile 4 with diisobutylaluminium hydride [ 23 ] and subsequent reoxidation of the intermediate aldehyde 5 with silver oxide, formed in situ from silver nitrite and sodium hydroxide [ 24 ], carboxylic functional group was introduced into the molecule. This three-step sequence afforded the desired acid 6 with higher overall yield than the published procedure based on lithiation and subsequent reaction of organolithium intermediate with carbon dioxide [ 19 ].…”
Section: Resultsmentioning
confidence: 99%
“…In the molecule of 4-(benzyloxy)-1-bromonaphtalene ( 3 ), the bromine atom was first replaced by nitrile functional group in Rosenmund – von Braun reaction [ [21] , [22] ]. By the reduction of formed nitrile 4 with diisobutylaluminium hydride [ 23 ] and subsequent reoxidation of the intermediate aldehyde 5 with silver oxide, formed in situ from silver nitrite and sodium hydroxide [ 24 ], carboxylic functional group was introduced into the molecule. This three-step sequence afforded the desired acid 6 with higher overall yield than the published procedure based on lithiation and subsequent reaction of organolithium intermediate with carbon dioxide [ 19 ].…”
Section: Resultsmentioning
confidence: 99%