Ammonia → Ethyl 3-oxovalerate

HRID 1614041Notes

Reaction equation

HRID 1614041 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[OH-].[Ca+2].[OH-].[C:13](Cl)(=O)CC.N>C(Cl)Cl.C(C(C)=O)C>[C:3]([CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH2:5][CH3:13]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8868Ethyl AcetoacetateHCID 62324Propionyl chlorideHCID 6093208Calcium Hydroxide

Product 1

HCID 78656Ethyl 3-oxovalerateYield 92.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Under the same conditions as in Example 1, 130 g (1.0 mol) of ethyl acetoacetate in a mixture of 1.2 l of methylene chloride and 300 ml of methyl ethyl ketone were reacted with 77.8 g (1.05 mol) of calcium hydroxide and 106.5 g (1.15 mol) of propionyl chloride. The subsequent reaction time after the ammonia had been metered in was 4 hours at a pH of 9.3. This gave 134 g (GC purity 72.0%) of ethyl propionylacetate (yield 67.0%).

Sources & evidence

ORD record
ord-87092ffea5e44cf0a1be212b3a263bbd
Source dataset
uspto-grants-1993_03
Patent number
US05194671

Reaction notes

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