ChemicalBook CAS DataBase List TRANS-3-HEXEN-1-OL

TRANS-3-HEXEN-1-OL synthesis

12synthesis methods

Product Name:TRANS-3-HEXEN-1-OL
CAS Number:544-12-7
Molecular formula:C6H12O
Molecular Weight:100.16

13894-61-6 Synthesis

13894-61-6
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544-12-7
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111-27-3 Synthesis

111-27-3
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Yield:111-27-3 35 %Spectr. ，544-12-7 65 %Spectr.

Reaction Conditions:

with methanol;tris((2-(diphenylphosphino)ethyl)amino)ruthenium monocarbonyl;hydrogen in toluene; under 45004.5 Torr; for 18 h;Glovebox;Inert atmosphere;Autoclave;Heating;Sealed tube;

Steps:

II.II.12 11.12 Hydrogenation of unsaturated esters (methyl trans-3-hexenoate) catalyzed by Ru(L)CO with methanol as activator

In a dry argon filled glove box, a ca. 80 mL Premex stainless steel autocalve fitted with a PTFE inner chamber and a PTFE coated magnetic stirring bar was charged with the complex Ru(L)CO (0.006 mmol), methyl trans-3-hexenoate (0.6 mmol) and toluene (6 mL). Methanol was added (0.05 mL) and the autoclave was sealed. The argon atmosphere in the autoclave was re- placed with H₂ by twice pressurization to 30 bar, and pressure release at room temperature. The autoclave was then pressurized with H₂ gas (60 bar). The solution was heated at 130 °C (heating mantel temperature) with stirring for 18 hrs. After cooling to 0 °C, the system was vented carefully and purged for 1 minute with argon. The conversion of starting material was an- alyzed by GC on an Agilent Technologies 6890N gas chromatography system equipped with a FID detector and an Agilent Technologies DB-1 capillary column (30 m x 0.250 mm / 1 .0 pm). Another sample (0.1 mL) was diluted with CDC (0.6 mL) in an NMR tube and analyzed by ¹H- NMR. Full conversion of the starting material was measured, to a mixture of ca. 65 % hex-3-en- 1 -ol, and ca. 35 % 1 -hexnaol (as well as methanol).

References:

WO2019/138000,2019,A1 Location in patent:Page/Page column 33