HRID465151

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

结构：CCCc1c(OCCCOc2ccc3ccc(OCCCC(=O)OC)cc3c2C(C)=O)ccc(C(C)=O)c1O

HCID54002660

未命名化合物

PRODUCTS

生成物

结构：CC(=O)c1ccc(OCCCOc2ccc3ccc(OCCCC(=O)O)cc3c2C(C)=O)c(CCCO)c1

HCID20232744

未命名化合物

收率 64%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

A mixture of 1.44 g of 4-[[8-acetyl-7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester and 27 ml of 1N sodium hydroxide in 54 ml of methanol was stirred at reflux for an hour. The methanol was removed in vacuo and the clear solution was acidified to pH 3. The precipitate was extracted with chloroform and dried. The resulting semi-solid was purified by flash column chromatography (eluting with 2% methanol/ethylacetate) to yield 0.9 g (64%) of 4-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxypropylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid of mp 121°-124°.

WORKUP

后处理

temperatureat reflux for an hour
customThe methanol was removed in vacuo
extractionThe precipitate was extracted with chloroform
customdried
customThe resulting semi-solid was purified by flash column chromatography (eluting with 2% methanol/ethylacetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4c19bcd1f2414210929c8d094fa714ca
来源数据集: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04550190
来源说明: uspto-grants-1985_10

反应 SMILES

C[O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:36](=[O:38])[CH3:37])[C:12]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25](O)[C:24]=3[CH2:33][CH2:34][CH3:35])=[CH:13][CH:14]=2)[CH:9]=1.[OH-:40].[Na+]>CO>[C:36]([C:11]1[C:12]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][C:24]=2[CH2:33][CH2:34][CH2:35][OH:40])=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[C:8]([O:7][CH2:6][CH2:5][CH2:4][C:3]([OH:2])=[O:39])[CH:17]=[CH:16]2)(=[O:38])[CH3:37]