Acetic Anhydride → HCID 4767934, compound

HRID 2260752Notes

Reaction equation

HRID 2260752 reaction equation
[CH:1](=O)[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:14]([NH:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:16])[CH3:15].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>>[C:14]([NH:17][C:18](=[CH:1][C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1)[C:19]([OH:21])=[O:20])(=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 8655SyringaldehydeHCID 10972AcetylglycineHCID 517045Sodium Acetate

Product 1

HCID 4767934HCID 4767934, compoundYield 31.7%

Conditions

Temperature
90 °C

Procedure

A 1.8 g (9.88 mmol) of syringaldehyde, 1.4 g (12.0 mmol) of N-acetylglycine, 1 g (12.2 mmol) of sodium acetate and 5 ml of acetic anhydride were stirred at 120° C. for 6 hours. A precipitate was washed with water and ethanol in this order and dried under reduced pressure. To the product was added 80 ml of 0.1N hydrochloric acid, and the mixture was stirred at 90° C. for 1 hour. A crystal formed was washed with water and acetone in this order to give 880 mg (yield 31.7%) of objective αacetylamino-3,5-dimethoxy-4-hydroxycinnamic acid.

Workup

  1. washA precipitate was washed with water and ethanol in this order
  2. customdried under reduced pressure
  3. additionTo the product was added 80 ml of 0.1N hydrochloric acid
  4. customA crystal formed
  5. washwas washed with water and acetone in this order

Sources & evidence

ORD record
ord-2f23e983c60a4576af9eb206b4d653da
Source dataset
uspto-grants-1995_12
Patent number
US05478856

Reaction notes

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