Hydrochloric Acid → 2-Propenoic acid, 3-[4-(acetyloxy)-3-methoxyphenyl]-

HRID 1866129Notes

Reaction equation

HRID 1866129 reaction equation
[C:1]([OH:14])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].Cl.C(OCC)(=O)C>N1C=CC=CC=1>[C:15]([O:10][C:9]1[CH:11]=[CH:12][C:4](/[CH:3]=[CH:2]/[C:1]([OH:14])=[O:13])=[CH:5][C:6]=1[O:7][CH3:8])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 445858Ferulic Acid

Product 1

HCID 53546772-Propenoic acid, 3-[4-(acetyloxy)-3-methoxyphenyl]-Yield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ferulic acid (5 g, 25.75 mmoles) in pyridine (75 ml) cooled to 0° C. and sheltered from light, acetic anhydride (13.14 g, 128.7 mmoles) is added in small aliquots. When the addition is ended the temperature is let reach the room value maintaining the solution under magnetic stirring for 24 hours. HCl 18.5% (160 ml) is added up to pH 2, one extracts with ethyl acetate and the organic phase is anhydrified and the solvent is evaporated at a reduced pressure. 5.15 g of trans-3-[4-acetyloxy-3-methoxyphenyl]-2-propenoic acid are obtained as a white solid. M.p. 199-205° C. Yield 85%.

Workup

  1. additionis added in small aliquots
  2. additionWhen the addition
  3. temperaturemaintaining the solution
  4. customthe solvent is evaporated at a reduced pressure

Sources & evidence

ORD record
ord-e5fb1e1cf2684ce68d5f5e59e282dcd3
Source dataset
uspto-grants-2009_12
Patent number
US07629368B2

Reaction notes

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