4-(HYDROXYMETHYL)PHENYL ISOBUTYRATE synthesis
- Product Name:4-(HYDROXYMETHYL)PHENYL ISOBUTYRATE
- CAS Number:70362-64-0
- Molecular formula:C11H14O3
- Molecular Weight:194.23
120464-79-1
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Yield:70362-64-0 83%
Reaction Conditions:
with sodium tetrahydroborate in tetrahydrofuran at 0 - 20;Inert atmosphere;
Steps:
Representative procedure for the preparation of intermediates 3a - i.
General procedure: 4-(hydroxymethyl)phenyl propionate (3b) is used as an example. To a solution of 2b (1.45 g, 8.14 mmol) in THF (40 mL) at 0 oC was added NaBH4 (0.462 g, 12.2 mmol). The reaction mixture was warmed to room temperature and stirred until the starting material was consumed (monitored by TLC). After 1 h, the reaction was diluted with EtOAc and quenched with aqueous NH4Cl. The aqueous layer was extracted with EtOAc (2) and the combined organic layers were subsequently washed with H2O and brine, and concentrated in vacuo. The resulting residue was purified by column chromatography (hexanes/EtOAc, 3:1) to provide compound 3b as a colorless oil.
References:
Zakhari, Joseph S.;Kinoyama, Isao;Hixon, Mark S.;Di Mola, Antonia;Globisch, Daniel;Janda, Kim D. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 21,p. 6203 - 6209] Location in patent:supporting information; experimental part
![Propanoic acid, 2-methyl-, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]phenyl ester](/CAS/20210305/GIF/1352347-92-2.gif)
1352347-92-2
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623-05-2
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123-08-0
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