Sulfuric Acid → Ethyl 2-acetyl-4-(2-methylphenyl)-3-oxobutanoate

HRID 26227

Reaction equation

HRID 26227 reaction equation
[Mg].[O:2]=[C:3]([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19](Cl)=[O:20].S(=O)(=O)(O)O>CCOCC.C(Cl)(Cl)(Cl)Cl.C(O)C>[C:3]([CH:4]([C:19](=[O:20])[CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:2])[CH3:10]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 8868Ethyl AcetoacetateHCID 2760632o-Tolyl-acetyl chlorideHCID 5462224Magnesium

Product 1

HCID 21325237Ethyl 2-acetyl-4-(2-methylphenyl)-3-oxobutanoate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

This material was prepared according to the procedure of M. Viscontini and N. Merckling, Helvetica Chimica Acta, 35, 2280 (1952). To 2.65 parts of magnesium turnings was added 15 parts absolute ethanol at room temperature and 0.5 parts of carbon tetrachloride. As soon as the initial reaction subsides 100 parts of dry ether was added. The mixture was stirred without cooling until the reaction ceased, then 19.6 parts of ethyl 3-oxobutanoate in 20 parts of dry ether was added with ice cooling and good stirring. After the resulting precipitate dissolved, the solution was cooled in an ice-salt bath and 16 parts of 2-methylphenylacetyl chloride was slowly added. The mixture was allowed to stand overnight at room temperature and then combined with ice and sulfuric acid. The ether layer was separated, washed with water, dried over sodium sulfate and stripped to give ethyl 2-acetyl-4-(2-methylphenyl)-3-oxobutanoate as a crude oil.

Workup

  1. customThis material was prepared
  2. additionwas added
  3. temperaturewithout cooling until the reaction
  4. dissolutionAfter the resulting precipitate dissolved
  5. temperaturethe solution was cooled in an ice-salt bath
  6. customThe ether layer was separated
  7. washwashed with water
  8. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-7baf14ecd86f45f5a549cee5a5e5b9b4
Source dataset
uspto-grants-1979_04
Patent number
US04148918

Linked notes

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