Benzene → HCID 14897398, compound

HRID 1464592Notes

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>>[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

Reactant 2

HCID 241Benzene

HCID 12192Ethyl diazoacetate

Product 1

HCID 14897398HCID 14897398, compoundYield 81%

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); 1H NMR (CDCl3) δ6.6 (m, 2H), 6.2 (m, 2H), 5.3 (m, 2H), 4.2 (q, 2H OCH2CH3), 2.5 (t, 1H), 1.3 (t, 3H CH2CH3)

Workup

customthe solvent was removed
distillationthe oily residue distilled in vacuo

Sources & evidence

ORD record: ord-3809dcd45be649e3bbd3ca9dc06aad86
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306718

Reaction notes

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