Sulfuric Acid → HCID 13157028, compound
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:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.S(=O)(=O)(O)O>C(O)C.ClC(Cl)(Cl)Cl>[C:13]([CH:3]([C:4]([CH3:6])=[O:5])[C:2]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
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 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 benzoyl 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-benzoylacetoacetate were obtained.
Workup
- temperatureat reflux temperature
- temperatureafter which the mixture was cooled
- stirringStirring
- waitwas continued for a further 4 hours at room temperature
- customhydrolysis
- customThe organic phase was separated off
- customdried
- customevaporated down under reduced pressure
Sources & evidence
- ORD record
- ord-2ad2235c18c24c37aa93a5b3b49eec8f
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05338639
Reaction notes
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