Sulfuric Acid → HCID 15496136, compound

HRID 1742169Notes

Reaction equation

HRID 1742169 reaction equation
[Mg].[C:2]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].[C:13](Cl)(=[O:15])[CH3:14].S(=O)(=O)(O)O>C(O)C.ClC(Cl)(Cl)Cl>[C:4]([CH:3]([C:13]([CH3:14])=[O:15])[C:2]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:5])[CH3:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 15538Tert-butyl acetoacetateHCID 5462224Magnesium

Product 1

HCID 15496136HCID 15496136, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

5 ml of tetrachloromethane were added to 24.3 g (1 mol) of magnesium turnings in 50 ml of dry ethanol under nitrogen and in the absence of moisture. After the beginning of gas evolution, a solution of 177.7 g (1 mol) of tert-butyl acetoacetate in 100 ml of dry ethanol was slowly added dropwise, the reaction mixture being kept at the reflux temperature. Stirring was carried out for a further 4 hours at this temperature, after which the mixture was cooled. 78.5 g (1 mol) of acetyl chloride was slowly added dropwise at 10° C. Stirring was continued for a further 4 hours at room temperature and hydrolysis was then effected with a mixture of 450 ml of ice-water and 25 ml of concentrated sulfuric acid. The organic phase was separated off, dried, and evaporated down under reduced pressure. 192.3 g of >96% pure tert-butyl 2-acetylacetoacetate were obtained.

Workup

  1. temperatureafter which the mixture was cooled
  2. stirringStirring
  3. waitwas continued for a further 4 hours at room temperature
  4. customhydrolysis
  5. customThe organic phase was separated off
  6. customdried
  7. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-1731fa52be8047318f8d4fb09fce3bc5
Source dataset
uspto-grants-1994_08
Patent number
US05338639

Reaction notes

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