Hydrochloric Acid → 4-Methoxycinnamate methyl ester

HRID 267671Notes

Reaction equation

HRID 267671 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH3:15]O>>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:15])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 132454-Methoxy cinnamic acid

Product 1

HCID 928414-Methoxycinnamate methyl ester

Procedure

p-Methoxycinnamic acid was dissolved in refluxing methanol containing a catalytic amount of hydrogen chloride to form methyl p-methoxycinnamate. The yield of purified ester was 85%, m.p. 88°-89° (lit. 90°; Dictionary of Organic Compounds, II, Sir Ian Heilbron, ed., p. 600 (1946)): λmaxCCl4 3.32, 3.38 and 3.52 (CH1 --OCH3), 5.81 (C=O), 6.1 and 10.15 (CH-CH, trans), 7.95 and 8.5--8.6 (ester)μ. The NMR (δ) supported the expected structure: 6.13-7.78 (series of multiples, aromatic and vinyl), 3.86 (--CO2CH3), and 3.78 (Ar--O--CH3).

Sources & evidence

ORD record
ord-835901e545fe4794893f06423d3a7c96
Source dataset
uspto-grants-1976_03
Patent number
US03943943

Reaction notes

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