Ammonia → Methyl 4-methyl-3-oxopentanoate

HRID 1614037Notes

Reaction equation

HRID 1614037 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2]C(C)=O.[OH-].[Ca+2].[OH-].[C:12](Cl)(=[O:16])[CH:13]([CH3:15])[CH3:14].N>C(Cl)Cl.C(C(C)=O)C>[C:12]([CH2:2][C:1]([O:7][CH3:8])=[O:6])(=[O:16])[CH:13]([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7757Methyl acetoacetateHCID 62325Isobutyryl chlorideHCID 6093208Calcium Hydroxide

Product 1

HCID 2759969Methyl 4-methyl-3-oxopentanoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Under the same conditions as in Example 1, 116 g (1.0 mol) of methyl acetoacetate in a mixture of 520 ml of methylene chloride and 30 ml of methyl ethyl ketone were reacted with 77.8 g (1.05 mol) of calcium hydroxide and 122.6 g (1.15 mol) of isobutyryl chloride. The pH in the subsequent reaction with ammonia was adjusted to 9.2. This gave 136 g (GC purity 79.8%) of methyl isobutyrylacetate (yield 75.4%).

Sources & evidence

ORD record
ord-ab77765be8944e4997d4f1b8178e6ac5
Source dataset
uspto-grants-1993_03
Patent number
US05194671

Reaction notes

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