HRID2164954

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

结构：CCCc1c(OCCOCCOCCOCCOc2c(C(C)=O)ccc(OCC(=O)OCC)c2CCC)ccc(C(C)=O)c1O

HCID14329981

未命名化合物

PRODUCTS

生成物

结构：CCCc1c(OCCOCCOCCOCCOc2c(C(C)=O)ccc(OCC(=O)O)c2CCC)ccc(C(C)=O)c1O

HCID14329980

未命名化合物

收率 66%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

A solution of 1.25 g (0.002 mole) of [4-acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid ethyl ester in 30 ml of methanol and 10 ml (0.01 mole) of 1.0N sodium hydroxide was stirred at reflux for 5 hours. Most of the solvent was removed in vacuo and the pH of the residue was adjusted to 2.0 with 6N hydrochloric acid. The product was extracted with methyl acetate and the dried (magnesium sulfate) extract was concentrated in vacuo to an oil which was purified by chromatography on 75 g of silica gel. Elution with toluene-ethyl acetate-acetic acid (65:25:10) gave 0.79 g (66% yield) of [4-acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid as an oil.

WORKUP

后处理

temperatureat reflux for 5 hours
customMost of the solvent was removed in vacuo
extractionThe product was extracted with methyl acetate
dry with materialthe dried (magnesium sulfate)
extractionextract
concentrationwas concentrated in vacuo to an oil which
customwas purified by chromatography on 75 g of silica gel
washElution with toluene-ethyl acetate-acetic acid (65:25:10)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1fb0c8a8ace34515bcc47dc16dcd11d8
来源数据集: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04507498
来源说明: uspto-grants-1985_03

反应 SMILES

C([O:3][C:4](=[O:45])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O: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:8]=1[CH2:42][CH2:43][CH3:44])C.[OH-].[Na+]>CO>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:45])=[O:3])=[C:8]([CH2:42][CH2:43][CH3:44])[C:9]=1[O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O: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:15])[CH3:14]