2-Propen-1-ol, 3-(2-methylphenyl)-, (2E)- synthesis
- Product Name:2-Propen-1-ol, 3-(2-methylphenyl)-, (2E)-
- CAS Number:501922-06-1
- Molecular formula:C10H12O
- Molecular Weight:148.2
24393-48-4
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501922-06-1
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Yield:501922-06-1 96%
Reaction Conditions:
Stage #1: ethyl trans-2-methylcinnamatewith diisobutylaluminium hydride in dichloromethane;toluene at -30; for 3 h;Inert atmosphere;
Stage #2: with water;rochelle salt in ethanol;dichloromethane;toluene;
Steps:
4.3. General procedure for the synthesis of alcohols 3a-f
General procedure: To a solution of the corresponding acrylic ester (1 equiv) in dry CH2Cl2 (5 mL per 1 mmol of ester), under argon, cooled to-30 °C, diisobutylaluminium hydride (1.2 M solution in toluene, 2 equiv) was added dropwise. The reaction mixture was stirred for 3 h at -30 °C. Ethanol (2 mL per 1 mmol of ester) was added followed by a saturated aqueous solution of potassium sodium tartrate (Rochelle salt, 3 mL per 1 mmol of ester). The layers were separated and the aqueous phase washed three times with DCM. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure.
References:
Knezevic, Anamarija;Landek, Goran;Dokli, Irena;Vinkovic, Vladimir [Tetrahedron Asymmetry,2011,vol. 22,# 9,p. 936 - 941] Location in patent:experimental part
1587-04-8
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