HRID2231499

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1140

Toluene

C7H8

HCID8857

Ethyl acetate

C4H8O2

结构：CCCc1c(OCCCCOCCCCOc2c(C(C)=O)ccc(OCCCC(=O)OCC)c2CCC)ccc(C(C)=O)c1O

HCID14329992

未命名化合物

PRODUCTS

生成物

结构：CCCc1c(OCCCCOCCCCOc2c(C(C)=O)ccc(OCCCC(=O)O)c2CCC)ccc(C(C)=O)c1O

HCID14329991

未命名化合物

收率 90%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID14798

Sodium Hydroxide

HNaO

PROCEDURE

实验过程

A solution of 2.71 g of 4-[4-acetyl-3-[4-[4-(4acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]butanoic acid ethyl ester in 20 ml of 1.0N sodium hydroxide and 90 ml of methanol was stirred at reflux for 6.5 hours. The methanol was removed in vacuo and the residue was acidified. The product was extracted with ether and the dried (magnesium sulfate) extract was concentrated in vacuo to an oil. Chromatography on 150 g of silica gel and elution with a solvent mixture of 5% acetic acid: 70% toluene: 25% ethyl acetate gave 2.32 g (90% yield) of 4-[4-acetyl-3-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]butanoic acid as an oil.

WORKUP

后处理

temperatureat reflux for 6.5 hours
customThe methanol was removed in vacuo
extractionThe product was extracted with ether
dry with materialthe dried (magnesium sulfate)
extractionextract
concentrationwas concentrated in vacuo to an oil
washChromatography on 150 g of silica gel and elution
additionwith a solvent mixture of 5% acetic acid

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-38f22043f60d437d9ef16a85c61562f4
来源数据集: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04782176
来源说明: uspto-grants-1988_11

反应 SMILES

C([O:3][C:4](=[O:45])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[C:31]([OH:38])[C:30]=2[CH2:39][CH2:40][CH3:41])[C:10]=1[CH2:42][CH2:43][CH3:44])C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH-].[Na+].CO>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:45])=[O:3])=[C:10]([CH2:42][CH2:43][CH3:44])[C:11]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[C:31]([OH:38])[C:30]=1[CH2:39][CH2:40][CH3:41])(=[O:17])[CH3:16]