ChemicalBook CAS DataBase List (R)-4-Chloro-3-hydroxybutyronitrile

(R)-4-Chloro-3-hydroxybutyronitrile synthesis

8synthesis methods

Product Name:(R)-4-Chloro-3-hydroxybutyronitrile
CAS Number:84367-31-7
Molecular formula:C4H6ClNO
Molecular Weight:119.55

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96-23-1 Synthesis

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Yield:84367-31-7 96.3%

Reaction Conditions:

with sodium hydroxide;Escherichia coli JM₁₀₉/pST₁₁₁ (FERM ABP-10922) in water; pH=7.5 - 7.6 at 20; for 23 h;Product distribution / selectivity;

Steps:

I.4.ii
To a 300 ml four-necked flask equipped with a pH electrode and an alkali feeding pipe controlled by a pH controller, 127.55 g of water and 4.41 g of HCN (0.1632 mol) were added. The pH of this solution was adjusted to 7.5 with 0.65 g of 30% NaOH (0.0049 mol). 10.00 g of 1,3-dichloro-2-propanol (0.0775 mol) was added thereto and agitated to give a homogeneous solution. Then, 20.00 g of the cell suspension with halohydrin epoxidase activity prepared in i) above was added to the flask, and the reaction was started at 20°C. The pH controller was set to feed 30% NaOH so that the pH in the system is maintained at 7.5-7.6. By supplying 1,3-dichloro-2-propanol and HCN at almost equimolar ratios relative to the NaOH fed, the concentrations of 1,3-dichloro-2-propanol and HCN in the system were controlled below 0.5 mol/kg and 1.1 mol/kg, respectively. After 23 hr, 4-chloro-3-hyroxybutyronitrile was accumulated at 0.753 mol/kg, The optical purity thereof was 94.8% ee ((R) enantiomeric excess). The yield from the 1,3-dichloro-2-propanol consumed in the reaction was 96.3%. This reaction solution was adjusted to pH 5.0 with hydrochloric acid, and HCN was removed at 60°C under reduced pressure (140 Torr) for 11 hr. Then, the HCN within the system was titrated with silver nitrate to thereby confirm that HCN concentration was 1 ppm or less.

References:

Mitsubishi Rayon Co. Ltd. EP2096103, 2009, A1 Location in patent:Page/Page column 19-20

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