Benzene → HCID 14897398, compound

HRID 374762Notes

Reaction equation

HRID 374762 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[CH:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:12][CH:11]=[CH:10][CH:9]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 241BenzeneHCID 12192Ethyl diazoacetate

Product 1

HCID 14897398HCID 14897398, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Ethyl diazoacetate (43.4 g, 0.38 mol) was added slowly (syringe pump) over a period of 7 hours to a mixture of benzene (594.32 g, 7.61 mol) and tetrakis (perfluorobenzoato) dirhodium(II) (0.84 g, 0.16 mol). After stirring at room temperature for 6 hours, the solvent was removed and the oily residue distilled in vacuo to give 50.44 g (81%) of ethyl 1,3,5-cycloheptatriene-1-carboxylate: bp 90°-96° C. 2.4-3.0 mm Hg);

Workup

  1. customthe solvent was removed
  2. distillationthe oily residue distilled in vacuo

Sources & evidence

ORD record
ord-6e98a46b222a45299b7736608156861f
Source dataset
uspto-grants-1996_01
Patent number
US05482938

Reaction notes

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