Methyl iodide → Methyl 3-(4-formylphenyl)-2-propenoate

HRID 986547Notes

Reaction equation

HRID 986547 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:14])=[O:10])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 980772-Propenoic acid, 3-(4-formylphenyl)-

Product 1

HCID 53401287Methyl 3-(4-formylphenyl)-2-propenoateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-formylcinnamic acid (7.04 g, 40 mmole), anhydrous potassium carbonate (16.5 g, 120 mmole) and methyl iodide (8.5 g, 60 mmole) in dry N,N-dimethylformamide (50 ml) was stirred overnight at room temperature and the solvent evaporated in vacuo. The product was partitioned between ether and water and the organic phase washed with brine and dried (MgSO4). Evaporation gave 7.32 g (97%) of the title ester of mp (aqueous methanol) 83°-85° C., νmax (mull) 1723, 1683, 1635 cm-1, δ(CDCl3) 3.83 (3H, s, CH3), 6.52 (1H, d, J15 Hz, C=CHCO2), 7.75 (1H, d, J 15 Hz, ArCH=C), 7.79 (4H, ABq, J 6 Hz, Δν16.5 Hz, arom), 10.08 (1H, s, CHO).

Workup

  1. customthe solvent evaporated in vacuo
  2. customThe product was partitioned between ether and water
  3. washthe organic phase washed with brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation

Sources & evidence

ORD record
ord-5f550cae348a47e7bcc3894b3e34a98c
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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