4-Hydroxybenzaldehyde → 4-[(2-Methyl-5-oxo-1,3-oxazol-4(5H)-ylidene)methyl]phenyl acetate

HRID 2292856Notes

Reaction equation

HRID 2292856 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([NH:13][CH2:14][C:15]([OH:17])=[O:16])(=O)[CH3:11].[C:18]([O-])(=[O:20])[CH3:19].[Na+].C(OC(=O)C)(=O)C>>[C:18]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:14]2[C:15](=[O:16])[O:17][C:10]([CH3:11])=[N:13]2)=[CH:4][CH:3]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 517045Sodium Acetate

Product 1

HCID 5395274-[(2-Methyl-5-oxo-1,3-oxazol-4(5H)-ylidene)methyl]phenyl acetateYield 89.8%

Conditions

Temperature
120 °C

Procedure

12.2 g of 4-hydroxybenzaldehyde, 13.9 g of N-acetylglycine, 15.6 g of sodium acetate, and 51.0 g of acetic anhydride were mixed, and the mixture was stirred at 120° C. for 5 hours. After the reaction, the reaction mixture was cooled to room temperature, and 50 ml of ice-water was added thereto, followed by stirring for 1 hour. The precipitated crystals were collected by filtration and washed with 100 ml of water. The resulting crystals were vacuum dried to give 22.0 g of 4-(4-acetoxybenzylidene)-2-methyloxazol-5(4H)-one as yellow crystals.

Workup

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. stirringby stirring for 1 hour
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with 100 ml of water
  6. customdried

Sources & evidence

ORD record
ord-1ef52abdf0ee4f669fe18c496f462297
Source dataset
uspto-grants-1997_11
Patent number
US05684186

Reaction notes

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