Dimethylformamide → Methyl cis-2-methoxy-5-methylcinnamate

HRID 615505Notes

Reaction equation

HRID 615505 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2.[OH-].[Na+].[CH3:15]I.CN(C)[CH:19]=[O:20]>O>[CH3:15][O:8][C:9]1[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][C:4]=1/[CH:5]=[CH:6]\[C:7]([O:20][CH3:19])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 70926-MethylcoumarinHCID 14798Sodium Hydroxide

Product 1

HCID 70480073Methyl cis-2-methoxy-5-methylcinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 6.0 g (37.46 mmol) of 6-methylcoumarin in 100 ml of dimethylformamide was treated with 3.29 g (82.41 mmol) of sodium hydroxide in 10 ml of water. After 15 minutes, 26.6 g (187.3 mmol) of methyl iodide was added. After an additional 6 hours, ether extraction provided the title compound as an oil. NMR in CDCl3 (δ units): 2.28 (singlet, 3); 3.66 (singlet, 3); 3.79 (singlet, 3); 5.97 and 7.13 (doublet, J=12 Hz, 1); 6.76 (doublet, J=8 Hz, 1); 7.09 (broad doublet, 1); 7.35 (broad singlet, 1).

Workup

  1. waitAfter an additional 6 hours
  2. extractionether extraction

Sources & evidence

ORD record
ord-3f0508e2aad0493cb53eb52922ce6ca8
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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