Acetic Anhydride → 4-Acetoxy-alpha-methylcinnamic acid

HRID 579922Notes

Reaction equation

HRID 579922 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[C:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].O[ClH](O)(=O)=O>N1C=CC=CC=1>[C:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2191964-Hydroxy-alpha-methylcinnamic acid

Product 1

HCID 537282834-Acetoxy-alpha-methylcinnamic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 100 ml of pyridine was dissolved 18 g of refined 4-hydroxy-α-methylcinnamic acid synthesized in Referential Example 1, 20 g of acetic anhydride was dropped into the solution, and the reaction was carried out at room temperature with stirring for 2 hours. Then, the liquid reaction mixture was dropped in a 1% by weight aqueous solution of hydroxychloric acid, and the precipitated reaction product was recovered by filtration, washed with water, and dried to obtain 20 g of 4-acetoxy-α-methylcinnamic acid.

Workup

  1. additionwas dropped into the solution
  2. customwas carried out at room temperature
  3. customThen, the liquid reaction mixture
  4. customthe precipitated reaction product
  5. filtrationwas recovered by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-6377ed1d635549c7a3e1456608d8f922
Source dataset
uspto-grants-1988_06
Patent number
US04751018

Reaction notes

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