Acetone → Diethyl Isopropylidenesuccinate

HRID 895265Notes

Reaction equation

HRID 895265 reaction equation
[O-]CC.[K+].[C:5]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:17][C:18]([CH3:20])=O.C(Br)C>CN(C)C=O>[C:18](=[C:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([O:14][CH2:15][CH3:16])=[O:13])([CH3:20])[CH3:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6332Ethyl BromideHCID 31249Diethyl SuccinateHCID 23670592Potassium ethoxide

Product 1

HCID 251287Diethyl IsopropylidenesuccinateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

52.5 mmol of potassium ethoxide were suspended in 100 mL of N,N-dimethylformamide in a 250 mL round bottom flask. To this slurry, heated up to 60° C., a mixture of 50 mmol of diethyl succinate and 57.5 mmol of acetone was added dropwise in 10 minutes. The course of the reaction was detected by GC. After 60 minutes the reaction was completed with a conversion of 97.2% (determined by GC). Then 87.5 mmol of ethyl bromide were added to the reaction mixture at 60° C. The slurry was stirred for 60 minutes at 60° C. The reaction was complete, giving the product isomers with a yield of 95% (determined by GC).

Workup

  1. additionwas added dropwise in 10 minutes
  2. customgiving the product isomers with a yield of 95% (determined by GC)

Sources & evidence

ORD record
ord-0d49c6bdef4a4219959a91e7c4568ee2
Source dataset
uspto-grants-2005_07
Patent number
US06914153B2

Reaction notes

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