Benzene → HCID 14897398, compound

HRID 2226154Notes

Reaction equation

HRID 2226154 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, 00.16 mol). After stirring at room temperature for 16 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-80e87d0f8bdd4dfa80ddca7673bf2860
Source dataset
uspto-grants-1994_09
Patent number
US05346911

Reaction notes

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