Acetic Acid → 4-[(1E)-3-(Acetyloxy)-1-propen-1-yl]-2-methoxyphenol

HRID 867165Notes

Reaction equation

HRID 867165 reaction equation
C([O:4][C:5]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([CH2:11][CH:12]=[CH2:13])=[CH:9][CH:10]=1)(=O)C.[C:16]([OH:19])(=[O:18])[CH3:17]>>[C:16]([O:19][CH2:13]/[CH:12]=[CH:11]/[C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[C:6]([O:14][CH3:15])[CH:7]=1)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 7136(2-Methoxy-4-prop-2-enylphenyl) acetate

Product 1

HCID 128354304-[(1E)-3-(Acetyloxy)-1-propen-1-yl]-2-methoxyphenol

Procedure

A mixture of eugenol acetate (16 g,0.0777 mol) and mercuric acetate (44.5 g, 1.4 mol) in 160 ml of acetic acid was refluxed for 20 hr. After filtration, the acetic acid solution was poured into water (150 ml) and extracted with ether (200 ml). The etheral solution was washed successively with water, aqueous NaHCO3, saturated NaCl solution and dried (Na2SO4). The solvent was evaporated to give 18 g of coniferyl acetate. Subsequent reduction of the coniferyl acetate with Red-Al gave coniferyl alcohol.

Workup

  1. temperaturewas refluxed for 20 hr
  2. filtrationAfter filtration
  3. additionthe acetic acid solution was poured into water (150 ml)
  4. extractionextracted with ether (200 ml)
  5. washThe etheral solution was washed successively with water, aqueous NaHCO3, saturated NaCl solution
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7444acb56e3146819047587fbf5339b9
Source dataset
uspto-grants-1978_07
Patent number
US04103006

Reaction notes

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