1,2-Dimethoxyethane → Ethyl Acetoacetate

HRID 2052369Notes

Reaction equation

HRID 2052369 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][CH3:8])(=[O:5])[CH3:4].[H][H].C[O:12][CH2:13][CH2:14]OC>>[C:3]([O:6][CH2:7][CH3:8])(=[O:5])[CH2:4][C:13]([CH3:14])=[O:12]

Participants

5

Reactant 4

HCID 80711,2-Dimethoxyethane2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 8868Ethyl AcetoacetateYield 62%

Procedure

To a refluxing slurry of 2.5 g (52 mmol) of 50% sodium hydride in 150 ml of DME was added 1.14 g (13 mmol) of ethyl acetate in 20 ml of DME. After a reaction period of 1.5 hours, hydrogen evolution ceased (285 ml at STP, 12.7 mmol) and the reaction mixture was worked up as described above to give a 0.47 g (62%) of crude ethyl acetoacetate, which was identified by VPC.

Sources & evidence

ORD record
ord-fd774f5c8fad46d286808b32f0095ebb
Source dataset
uspto-grants-1980_01
Patent number
US04183931

Reaction notes

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