Styrene → Ethyl 2-phenylcyclopropane-1-carboxylate

HRID 247734Notes

Reaction equation

HRID 247734 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>C(Cl)Cl>[C:3]1([CH:2]2[CH2:1][CH:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7501Styrene2×HCID 12192Ethyl diazoacetate

Product 1

HCID 316914Ethyl 2-phenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In Example 4, a flask was charged with 1.0 g of the catalyst described in Example 1, CH2Cl2 (2.5 mL), and styrene (2.5 mL). A solution of ethyl diazoacetate (0.23 g), CH2Cl2 (12.5 mL), and styrene (12.5 mL) was added slowly dropwise and the resulting mixture was stirred for 24 hours. The reaction product was analyzed by gas chromatography and the catalyst recovered by filtration. This process was repeated for a total of ten cycles during which yields of ethyl 2-phenylcyclopropane-carboxylate remained essentially constant at about 91%. The recovered catalyst was dried in vacuo. Duplicate elemental analyses gave copper contents of the recovered catalyst of 1.83 and 1.88%.

Workup

  1. filtrationthe catalyst recovered by filtration

Sources & evidence

ORD record
ord-4239afc249914d91891f9b225d8f957a
Source dataset
uspto-grants-1987_11
Patent number
US04709085

Reaction notes

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