ChemicalBook CAS DataBase List 3-Phenyl-2-propen-1-ol

3-Phenyl-2-propen-1-ol synthesis

12synthesis methods

Product Name:3-Phenyl-2-propen-1-ol
CAS Number:4407-36-7
Molecular formula:C9H10O
Molecular Weight:134.18

103-26-4
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4407-36-7
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$18.00/25g

Yield:4407-36-7 93.9%

Reaction Conditions:

with methanol;diisobutylaluminium hydride in hexane;dichloromethane at -78 - 20; for 2 h;Inert atmosphere;

Steps:

1.II 1. Synthesis Process I
Step (II):
3-phenyl-acrylic acid, methyl ester (D011b, 4 g, 24.7 mmol, 1 eq) was added into a 500 ml round bottom flask filled with N₂ gas and was dissolved in anhydrous dichloromethane and then placed in a low-temperature reactor set at -78° C.
Diisobutylaluminium hydride 1M solution (DIBAL-H; 1M solution in hexane, 74 ml, 74.0 mmol, 3 eq) was slowly added dropwise over 30 minutes to the reaction solution and methanol (22 ml) was slowly added dropwise while the reaction temperature was raised to 0° C. and stirring was carried out for 1 hour.
The reaction solution was transferred to room temperature, stirred for 30 minutes and then a saturated aqueous solution of Rochelle's salt (88 ml) was added thereto.
The reaction mixture was vigorously stirred at room temperature for 2 hours, and the mixture was partitioned twice with dichloromethane (300 ml) and distilled water (300 ml) to collect the organic layers and was dehydrated with sodium sulfate, filtered and the resulting filtrate was concentrated under reduced pressure.
The concentrate was purified by silica gel column chromatography (ethyl acetate:n-hexane=3:1) to obtain the pure product 3-phenyl-pro-2-pen-1-ol (D011c, 3.1 g, yield=93.9%, Rf=0.37 (2:1 n-hexane-ethyl acetate) to apply to the next step.

References:

PRG S&TECH INC.;PARK, Bum Joon;SONG, Gyu Yong;O, Yu Seok;LEE, Jee Hyun;YUN, Eun Ju US2020/48274, 2020, A1 Location in patent:Paragraph 0051-0055

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