Acetone → Methyl p-ethoxycinnamate

HRID 267674Notes

Reaction equation

HRID 267674 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)=[O:4].[CH2:14](I)[CH3:15].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CO>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]=[CH:5][C:3]([O:2][CH3:1])=[O:4])=[CH:12][CH:11]=1)[CH3:15]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5319562Methyl-P-Coumarate

Product 1

HCID 53395761Methyl p-ethoxycinnamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This ester was treated with excess ethyl iodide in the presence of potassium carbonate in refluxing dry acetone for 48 hours. A moderate yield of methyl p-ethoxycinnamate was obtained as white crystals from methanol, mp 68--70° C: λmaxCCl4 5.8, 6.09, 6.22, 6.6, 8.0, 8.56, 9.53, 10.15, and 10.8 μ. Reduction of methyl p-ethoxycinnamate in benzene with LAH gave a 50% yield, after recrystallization from methanol, of p-ethoxycinnamyl alcohol, mp 85° C: λmaxCC14 2.75, 6.2, 6.61, 6.75, 8.93, 9.2, 9.55, 9.97, 10.3, 10.85, and 11.87 μ.

Sources & evidence

ORD record
ord-ed5cb049445e47af94a362502726c457
Source dataset
uspto-grants-1976_03
Patent number
US03943943

Reaction notes

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