ChemicalBook CAS DataBase List (R)-(-)-1,3-Butanediol

(R)-(-)-1,3-Butanediol synthesis

10synthesis methods

Product Name:(R)-(-)-1,3-Butanediol
CAS Number:6290-03-5
Molecular formula:C4H10O2
Molecular Weight:90.12

105-45-3
699 suppliers
$5.00/5g

6290-03-5
220 suppliers
$6.00/1g

3976-69-0 Synthesis

3976-69-0
329 suppliers
$6.00/5g

Yield: 99.2 % ee

Reaction Conditions:

with ruthenium trichloride;(R,R)-1,2-diphenylethylenediamine;potassium tert-butylate;hydrogen;(R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in isopropyl alcohol at 100; under 60006 - 75007.5 Torr; for 5 h;Sealed tube;

Steps:

1 Comparative Example 1: Preparation of (R)-1,3-butanediol by asymmetric hydrogenation of methyl acetoacetate
In the glove box, put RuCl3 (0.69mg, 0.0033mmol), (R)-BINAP (2.3mg, 0.0036mmol), (1R,2R)-1,2-diphenyl-1,2-ethylenediamine (0.78 mg, 0.0036mmol) and isopropanol (150g) were added to a single-necked flask equipped with a magnetic stirrer, the stirring was turned on, the metal precursor and the ligand were dissolved and coordinated for 30 minutes,Obtain the catalyst solution, seal the single-neck bottle, take it out of the glove box, and pump it into a 0.5L reactor with a flat flow pump under the protection of nitrogen. The reactor has been replaced with nitrogen in advance, and the substrate methyl acetoacetate (116g, 1mol) and Potassium tert-butoxide (0.12g).After the catalyst solution was added, the reactor was replaced with hydrogen for three times, 8MPa hydrogen was charged, and the reactor was turned on for stirring and heating.When the internal temperature of the reactor reaches 100°C, open the hydrogen gas inlet valve, keep the internal pressure of the reactor at 10MPa, start timing, keep the reaction for 5 hours, the flowmeter shows that the hydrogen absorption rate is less than 0.1mL/min, terminate the reaction, and cool the reactor To room temperature, sampling and GC analysis showed that the conversion rate of raw material methyl acetoacetate was 99.9%, and the selectivity of (R)-1,3-butanediol was 8.8%.The ee value is 99.2%, and the selectivity of (R)-3-hydroxybutyrate is 90.9%.

References:

CN112538095, 2021, A Location in patent:Paragraph 0088-0089

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24915-95-5 Synthesis