(R)-4-CHLORO-3-HYDROXYBUTYRIC ACID METHYL ESTER Chemical Properties

Boiling point:

248.6±20.0 °C(Predicted)

Density 

1.232±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

12.73±0.20(Predicted)

CAS DataBase Reference

88496-70-2(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

2918199890

(R)-4-CHLORO-3-HYDROXYBUTYRIC ACID METHYL ESTER Usage And Synthesis

Chemical Properties

Colorless liquid

Synthesis

The general procedure for the synthesis of (R)-4-chloro-3-hydroxybutanoic acid methyl ester from the compound (CAS:114819-45-3) is as follows: to a solution of (R)-3-hydroxybutanoic acid methyl ester (125.1 g, 0.93 mol) in methylene chloride (1.8 L) was added triphenylphosphine (244.5 g, 0.93 mol), and under cooling in an ice-water bath, the N- chlorosuccinimide (124.2 g, 0.93 mol) was added slowly under cooling in an ice water bath. The reaction mixture was stirred at 5 °C for 20 min, followed by continued stirring at room temperature for 18 h. The reaction was carried out at room temperature. Upon completion of the reaction, the solvent was removed by evaporation and the residue was purified by column chromatography (petroleum ether/ethyl acetate, 20:1 to 5:1, gradient elution) to afford the target product (R)-methyl (R)-4-chloro-3-hydroxybutanoate (33 g, three-step overall yield 26%). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.18-4.25 (m, 1H), 3.68 (s, 3H), 3.55-3.60 (m, 2H), 3.32-3.33 (d, J = 4.2 Hz, 1H), 2.52-2.68 (m, 2H).

References

[1] Patent: WO2007/21982, 2007, A2. Location in patent: Page/Page column 67-68

(R)-4-CHLORO-3-HYDROXYBUTYRIC ACID METHYL ESTER(88496-70-2)Related Product Information

• 3-Hydroxybutyric acid
• Methyl 4-chloro-3-hydroxybutyrate
• (R)-4-CHLORO-1,3-BUTANEDIOL
• Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate
• Methyl 4-chlorobutyrate
• 4-Chloro-3-hydroxy-butyricacidmethylester
• (R)-4-CHLORO-3-HYDROXYBUTYRIC ACID METHYL ESTER