Eugenol → (2-Methoxy-4-prop-2-enylphenyl) acetate

HRID 411874Notes

Reaction equation

[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH2:7][CH:8]=[CH2:9])[OH:3].[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(O)(=O)C>[C:13]([O:3][C:2]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]=[CH2:9])=[CH:10][C:1]=1[O:11][CH3:12])(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 140 °C

Procedure

Into a three-neck, 5000 ml round bottom flask equipped with an addition funnel, mechanical stirrer, condenser, thermometer, heating mantle and nitrogen inserting tube is charged eugenol (2,519 grams, 15.3 moles). The eugenol was heated to 75° C. The acetic anhydride (1554 grams, 15.2 moles) was added with stirring over a one-hour period. The reaction mixture was then heated to 140° C. and stirred for 3 hours. The acetic acid by-product from the acylation reaction was stripped from the reaction mixture at 36° C. and 0.15 mm Hg pressure. The reaction produced 3-(4-acetoxy-3-methoxyphenyl)propene (3134 grams, 99.3 percent yield.)

Workup

customInto a three-neck, 5000 ml round bottom flask equipped with an addition funnel, mechanical stirrer, condenser
temperaturethermometer, heating mantle and nitrogen inserting tube
stirringstirred for 3 hours
customwas stripped from the reaction mixture at 36° C.

Sources & evidence

ORD record: ord-c54a5f621832485ba4fd28577ec67db5
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559329B2

Reaction notes

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