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

HRID 1525371Notes

Reaction equation

HRID 1525371 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[C:12]([O-:15])(=[O:14])[CH3:13].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([O:9][C:8]1[CH:10]=[CH:11][C:3](/[CH:2]=[CH:13]/[C:12]([OH:15])=[O:14])=[CH:4][C:5]=1[O:6][CH3:7])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate

Product 1

HCID 53546772-Propenoic acid, 3-[4-(acetyloxy)-3-methoxyphenyl]-Yield 69.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a round bottomed flask, 30.04 g of vanillin (0.197 mol) and 26.0 g of sodium acetate (0.317 mol) were dissolved in 200 mL of acetic anhydride (2.12 mol). About 1 mL of pyridine was added to the flask and the mixture was heated to reflux. After 24 h, the brown solution was poured over about 500 g of crushed ice and the solution was stirred until the appearance of a yellow-brown solid. The flask was left overnight in the freezer and a dark yellow solid was obtained by filtration. The crude solid was recrystallized from acetic acid/water to give 32.3 g of a yellow beige solid in a 69% yield.

Workup

  1. temperaturethe mixture was heated to reflux
  2. waitThe flask was left overnight in the freezer
  3. customa dark yellow solid was obtained by filtration
  4. customThe crude solid was recrystallized from acetic acid/water

Sources & evidence

ORD record
ord-c604498052714895b6db8385d8863086
Source dataset
uspto-grants-2015_07
Patent number
US09080011B2

Reaction notes

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