Methyl acetoacetate → Methyl 3-oxoheptanoate

HRID 1614038Notes

Reaction equation

HRID 1614038 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[OH-].[Ca+2].[OH-].[C:12](Cl)(=O)[CH2:13][CH2:14]CC>C(Cl)Cl.C(C(C)=O)C>[C:3]([CH2:2][C:1]([O:7][CH3:8])=[O:6])(=[O:4])[CH2:5][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 7757Methyl acetoacetateHCID 61186Valeryl chlorideHCID 6093208Calcium Hydroxide

Product 1

HCID 546075Methyl 3-oxoheptanoateYield 95.5%

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 138.7 g (1.15 mol) of valeryl chloride. The pH in this gave 151 g (GC purity 82.5%) of methyl valerylacetate (yield 79.0%).

Sources & evidence

ORD record
ord-4ce5aded888644119cb3bf4666050e13
Source dataset
uspto-grants-1993_03
Patent number
US05194671

Reaction notes

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