合成路线:It can be prepared in two different ways:1) The condensation of 2,4-di-tert-butylphenol (I) with dimethyl acetylenedicarboxylate (II) by means of benzyltrimethylammonium hydroxyde (III) gives 2,4-di-tert-butylphenoxyfumaric acid dimethyl ester (VI),which is hydrolyzed with NaOH in refluxing methanol - water yielding the corresponding acid (V).Finally this acid is cyclized by treatment with chlorosulfonic acid.
合成路线:2) The Friedel-Crafts reaction of 2,4-di-tert-butylphenol (I) with acetic anhydride (VI) by means of BF3 gives 3,5-di-tert-butyl-2-hydroxyacetophenone (VII),which is cyclized with diethyl oxalate (VIII) by means of NaOEt in a refluxing mixture ethanol - ethyl ether to afford ethyl 6,8-di-tert-butyl-4-oxo-4H-1-benzopyran-2-carboxylate (IX) (1,2).Finally this compound is hydrolyzed with NaOH in ethanol (1).
参考文献标题:
文献作者:Cairns,H.; et al.
参考来源:GB 1368244
合成路线:It can be prepared in two different ways:1) The condensation of 2,4-di-tert-butylphenol (I) with dimethyl acetylenedicarboxylate (II) by means of benzyltrimethylammonium hydroxyde (III) gives 2,4-di-tert-butylphenoxyfumaric acid dimethyl ester (VI),which is hydrolyzed with NaOH in refluxing methanol - water yielding the corresponding acid (V).Finally this acid is cyclized by treatment with chlorosulfonic acid.
合成路线:2) The Friedel-Crafts reaction of 2,4-di-tert-butylphenol (I) with acetic anhydride (VI) by means of BF3 gives 3,5-di-tert-butyl-2-hydroxyacetophenone (VII),which is cyclized with diethyl oxalate (VIII) by means of NaOEt in a refluxing mixture ethanol - ethyl ether to afford ethyl 6,8-di-tert-butyl-4-oxo-4H-1-benzopyran-2-carboxylate (IX) (1,2).Finally this compound is hydrolyzed with NaOH in ethanol (1).
参考文献标题:Terbucromil
文献作者:Castar,J.; Church,M.K.
参考来源:Drugs Fut 1978,3(11),841
产品链接: CAS No. 37456-21-6››