ChemicalBook CAS DataBase List (R)-(+)-BETA-CITRONELLOL

(R)-(+)-BETA-CITRONELLOL synthesis

11synthesis methods

Product Name:(R)-(+)-BETA-CITRONELLOL
CAS Number:1117-61-9
Molecular formula:C10H20O
Molecular Weight:156.27

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1117-61-9
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Yield:1117-61-9 99%

Reaction Conditions:

with BF₄^(1-)*C₉₀H₁₃₀O₆P₂Rh⁽¹⁺⁾;hydrogen in methanol at 20; under 22502.3 Torr; for 18 h;Autoclave;enantioselective reaction;Reagent/catalyst;Temperature;Pressure;

Steps:

12 Example XII Preparation of chiral Citronellol
In a 10 mL reaction tube was added phosphine ligand R-L3d (5.9 mg, 0.005 mmol) and rhodium (1,5-cyclooctadiene) rhodium tetrafluoroborate [Rh (C0D) 2] BF4 (2.lmg, (2 mL). The solution was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure to give a brown solid. After vacuum pumping for 2 hours, the solution was added with a solution of 30 mL of toluene, and this solution was added to a solution of Z-citral (38.lg, 250mmol, E / Z = 1/99,(Rh (R_L3d) (COD)] BF4 to citral in a molar ratio of 1/50000) was charged into an autoclave, and after six times of hydrogen substitution, the initial hydrogen pressure was 30 bar, 20 Lt; 0 & gt; C for 18 hours. Cooled, carefully vented, the autoclave was removed, the vial was removed, the solvent was removed, the conversion was checked by NMR, and the enantiomeric excess was determined by gas chromatography (column? -OH? 225). Yield 99%, R-enantiomeric excess 98%

References:

Wanhua Chemical Group Co.,Ltd.;zhang, Wan Bin;zhang, zhenfeng;chen, jianzhong;Bao, Yuan Ye;Dong, Jing;zhang, Yong Zhen;LI, Yuan CN105254474, 2016, A Location in patent:Paragraph 0077-0079

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2385-77-5 Synthesis