Methyl iodide → Methyl 2-(4-nitrophenyl)propionate

HRID 272742Notes

Reaction equation

HRID 272742 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH2:15]1OCCOCCOCCOCCOCCOC1.CI.[H-].[Na+]>CN(C=O)C>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([CH:4]([CH3:15])[C:3]([O:2][CH3:1])=[O:14])=[CH:10][CH:9]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 270191Methyl p-nitrophenylacetate

Product 1

HCID 3016521Methyl 2-(4-nitrophenyl)propionateYield 697.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (4-nitro-phenyl)-acetic acid methyl ester (3.0 g, 15 mmol), 18-crown-6 (396 mg, 1.5 mmol), and methyl iodide (3.74 mL, 60 mmol) were combined in DMF (50 mL) and cooled to 0° C. Sodium hydride (660 mg, 16.5 mmol) was added. The solution was stirred with warming to room temperature overnight. The solution was partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to provide 2.19 g (70%) of the title compound. MS (DCI) m/e 210 (M+H)+.

Workup

  1. temperaturewith warming to room temperature overnight
  2. customThe solution was partitioned between ethyl acetate and water
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d66c2f07b1af4951828b9ae4129239f5
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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