1-Butanol → n-butyl (S)-(-)-4-chloro-3-hydroxybutyrate

HRID 1647334Notes

Reaction equation

HRID 1647334 reaction equation
[Cl:1][CH2:2][C:3](=[O:12])[CH2:4][C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6].C(O)CCC>C(Cl)Cl>[Cl:1][CH2:2][C@@H:3]([OH:12])[CH2:4][C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6]

Participants

4

Reactant 2

HCID 2631-ButanolHCID 13705501Butyl 4-chloro-3-oxobutanoate

Product 1

HCID 13705504n-butyl (S)-(-)-4-chloro-3-hydroxybutyrateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 100 ml Hastelloy-made autoclave having been purged with nitrogen were charged 38.8 g (0.2 mol) of n-butyl 4-chloroacetoacetate and 50 ml of n-butyl alcohol, and solution of 73 mg of Ru2Cl2 [(R)-(+)-BINAP]2Et3N in 2 ml of methylene chloride was added thereto. The mixture was stirred at 100° C. under a hydrogen pressure of 11 to 12 kg/cm2 for 2 hours to conduct hydrogenation. The solvent was evaporated, and the residue was distilled under reduced pressure to give 35.0 g (percent yield: 90%) of n-butyl (S)-(-)-4-chloro-3-hydroxybutyrate.

Workup

  1. customhaving been purged with nitrogen
  2. additionwas added
  3. customThe solvent was evaporated
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-70389c81254d4ff99dc66cf10e7e23a7
Source dataset
uspto-grants-1995_07
Patent number
US05430171

Reaction notes

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