Acenaphthene → 1-o-Tolylbutane-1,3-dione

HRID 1578581Notes

Reaction equation

HRID 1578581 reaction equation
C=C1OC(=O)C1.C1C2=[C:18]3[C:13](=CC=C2)[CH:12]=[CH:11][CH:10]=[C:9]3[CH2:8]1.C1C2C3=C4C(=CC=2)C=CC=C4C=CC3=CC=1.COC1C=CC2C(=CC=C(OC)C=2)C=1.[Cl-].[Al+3].[Cl-].[Cl-].CC(=O)C(=O)C.[C:59](F)(=[O:64])[CH2:60][C:61]([CH3:63])=[O:62].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.ClCCCl>[C:9]1([CH3:8])[CH:18]=[CH:13][CH:12]=[CH:11][C:10]=1[C:59](=[O:64])[CH2:60][C:61](=[O:62])[CH3:63]

Participants

11

Reactant 7

HCID 6734Acenaphthene2×HCID 12661Diketene3×HCID 31423Pyrene2×HCID 796272,6-DimethoxynaphthaleneHCID 6451240Aluminum(III) ChlorideHCID 12336936HCID 12336936, compoundHCID 131710023HCID 131710023, compound

Product 1

HCID 142423511-o-Tolylbutane-1,3-dioneYield 6.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

In the reaction of diketene with aromatic compounds that are solid at room temperature, for example acenaphthene, pyrene, or 2,6-dimethoxynaphthalene, solvents have to be added which do not react with diketene. The aforesaid literature references do not contain any description of corresponding experiments. In proper experiments with 1,2-dichloroethane it has been found that with acenaphthene the yield is drastically reduced and resinifications do occur and that the aluminum chloride-butanedione complexes with pyrene have a high stability. If, however, the diketene is transformed into acetoacetyl fluoride which is then reacted with toluene in the presence of aluminum chloride in chloroform, a yield of 6.5 % only of 1-tolyl-butane-1,3-dione is obtained, calculated on the diketene (cf. G. A. Olah and S. J. Kuhn, J.Org. Chem. 26, page 225 (1961)).

Workup

  1. customat room temperature
  2. additionto be added which

Sources & evidence

ORD record
ord-27bae2eefb1541dfa17a1121c398e84d
Source dataset
uspto-grants-1976_02
Patent number
US03937737

Reaction notes

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