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| | (R)-4-CHLORO-3-HYDROXYBUTYRIC ACID METHYL ESTER Basic information |
| | (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) |
| 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 Preparation Products And Raw materials |
| Raw materials | Butanoic acid, 4-cyano-3-hydroxy-, methyl ester, (3S)--->Oxiraneacetic acid, methyl ester, (R)--->methyl 3,4-epoxybutyrate-->BUTANOIC ACID, 4-CYANO-3-HYDROXY-, METHYL ESTER, (3R)--->Butanoic acid, 3,4-dihydroxy-, methyl ester, (3R)--->4-Chloro-3-hydroxy-butyricacidmethylester-->METHYL (S)-4-CHLORO-3-HYDROXYBUTYRATE-->Triphenylphosphine-->Sodium cyanide-->Methyl 4-chloro-3-oxo-butanoate | | Preparation Products | (R)-(+)-3-Hydroxybutyrolactone-->L(-)-2-Octanol |
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