Ethyl Acetoacetate → HCID 22902405, compound

HRID 1489641Notes

Reaction equation

HRID 1489641 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH3:10][CH2:11][O-:12].[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:19](Cl)=[O:20]>C(O)C.O1CCCC1>[C:3]([C:2]([C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:16]([O:15][CH3:14])[CH:17]=1)([C:11]([CH3:10])=[O:12])[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

6

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 77070Veratroyl chlorideHCID 2723922Sodium ethoxide

Product 1

HCID 22902405HCID 22902405, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent4×HCID 8028TetrahydrofuranSolvent4×

Procedure

32 ml of ethyl acetoacetate were added dropwise with ice cooling to 100 ml of 21% strength sodium ethylate solution in ethanol (=solution I). After 20 minutes 75 ml of a solution of 50 g of 3,4-dimethoxybenzoyl chloride in 150 ml of tetrahydrofuran (=solution II) were added dropwise to the reaction mixture. Subsequently further quanities of solutions I and II were added dropwise to the reaction mixture alternately, each at intervals of 20 minutes, until the reaction mixture contained a total of 190 ml of solution I and 176 ml of solution II. After 16 hours the precipitated salts were filtered out, washed with tetrahydrofuran and then suspended in water. The aqueous mixture was acidified to pH 1 with ice cooling and was extracted with methyl tert-butyl ether. The extract was evaporated to dryness, and 45 g of ethyl 2-acetyl-2-(3,4-dimethoxybenzoyl)-acetoacetate were obtained as a yellow oil.

Workup

  1. customat intervals of 20 minutes
  2. filtrationAfter 16 hours the precipitated salts were filtered out
  3. washwashed with tetrahydrofuran
  4. extractionwas extracted with methyl tert-butyl ether
  5. customThe extract was evaporated to dryness

Sources & evidence

ORD record
ord-57ebecc578e14f6ebdf27456a4ceac5a
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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