Methyl iodide → Methyl 1-phenylcyclopropane-1-carboxylate

HRID 2275563Notes

Reaction equation

HRID 2275563 reaction equation
CI.[C:3]1([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)C>[C:3]1([C:9]2([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 802061-Phenylcyclopropanecarboxylic acid

Product 1

HCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (2.8 mL, 45.0 mmol) was added to a mixture of 1-phenylcyclopropanecarboxylic acid (4.9 g, 30.0 mmol) and potassium carbonate (8.3 g, 60.0 mmol) in DMF (50 mL) at room temperature and the reaction mixture was stirred for 1 h. Then the reaction mixture was diluted with diethyl ether. The resulting mixture was washed with water (×2) and brine successively, then dried and concentrated to afford the desired product.

Workup

  1. washThe resulting mixture was washed with water (×2) and brine successively
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8b8f3beff52f4d5f9423c8b670d01cde
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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