4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】47150

【品名】4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoic acid

【CA登记号】

【分子式】C₁₆H₁₆O₄

【分子量】272.30064

【元素组成】C 70.57% H 5.92% O 23.5%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

Ethyl ester (II) is alkylated with benzyl chloride (I) by means of K2CO3 in acetone to yield 4-benzyloxy derivative (III), which is then hydrolyzed with KOH in H2O/DMSO to provide carboxylic acid (IV). Depside formation between derivative (IV) and ethyl ester (II) by means of trifluoroacetic anhydride in toluene furnishes ethyl benzoate derivative (V), which is finally hydrogenated over Pd/C in AcOEt to yield the target product.

参考文献中间体

合成目标

【1】 Kumar, S.; Muller, K.; Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1.Novel analogues of barbatic and diffractaic acid. Eur J Med Chem 1999, 34, 12, 1035.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	19171	1-(Chloromethyl)benzene; Benzyl chloride	100-44-7	C₇H₇Cl	详情	详情
(II)	47148	ethyl 2,4-dihydroxy-3,6-dimethylbenzoate		C₁₁H₁₄O₄	详情	详情
(III)	47149	ethyl 4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoate		C₁₈H₂₀O₄	详情	详情
(IV)	47150	4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoic acid		C₁₆H₁₆O₄	详情	详情
(V)	47151	ethyl 4-[[4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoyl]oxy]-2-hydroxy-3,6-dimethylbenzoate		C₂₇H₂₈O₇	详情	详情

Extended Information