Ethyl 4-chloroacetoacetate → Butanoic acid, 4-chloro-3-hydroxy-, ethyl ester
Reaction equation
[Cl:1][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H][H]>C(O)C>[Cl:1][CH2:2][CH:3]([OH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
In a 200 ml-volume stainless steel-made autoclave whose atmosphere had been replaced with nitrogen were charged 8.23 g (50 mmoles) of ethyl 4-chloroacetoacetate and 20 ml of ethanol. To the mixture was added 84 mg (0.05 mmole) of Ru2Cl4 ((-)-BINAP)2 (C2H5)3N, and the mixture was heated to 100° C. When the temperature reached 100° C., 100 kg/cm2 of hydrogen was introduced into the autoclave, and the mixture was stirred under heating. After cooling to room temperature, the reaction mixture was taken out, and the ethanol was removed by distillation. Distillation of the residue gave 8.07 g (97) of ethyl 4-chloro-3-hydroxybutyrate having a boiling point of 74°-75° C./l mmHg).
Workup
- customreached 100° C.
- temperatureunder heating
- temperatureAfter cooling to room temperature
- customthe ethanol was removed by distillation
- distillationDistillation of the residue
Sources & evidence
- ORD record
- ord-1a18d63915d444e2a7705bff2e567dc3
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04895979
Reaction notes
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