Ethanol → HCID 10909935, compound

HRID 413512Notes

Reaction equation

HRID 413512 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H][H].C([OH:15])C>>[Cl:1][CH2:2][CH2:3][C@@H:4]([OH:15])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 69484Ethyl 4-chloroacetoacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 10909935HCID 10909935, compoundYield 94%

Conditions

Temperature
116 °C

Procedure

14 Kg of ethyl 4-chloro-3-oxobutyrate (titre 88%) and 6.2 g of {[Ru (p-cymene) I (+) TMBTP] I}, are placed under argon in a 200-liter reactor, in 143 l of ethyl alcohol. The mixture is heated at 116° C. and pressurized with hydrogen at 5-6 bar. Temperature rises up to 124° C. and the reaction goes to completion within about 1 hour. The mixture is cooled, concentrated at reduced pressure, and the residue, analyzed with gaschromatography, has a 81% titre of ethyl (+) (R)-4-chloro-3-hydroxybutyrate, with an e.e. of 96.7% reaction yield: 94%.

Workup

  1. customrises up to 124° C.
  2. temperatureThe mixture is cooled
  3. concentrationconcentrated at reduced pressure
  4. customwith an e.e. of 96.7% reaction yield: 94%

Sources & evidence

ORD record
ord-68592bc234b94b89b7fb9106b57e898c
Source dataset
uspto-grants-2003_05
Patent number
US06566552B2

Reaction notes

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