Vanillin → 5(4H)-Oxazolone, 4-[[4-(acetyloxy)-3-methoxyphenyl]methylene]-2-methyl-

HRID 259617Notes

Reaction equation

HRID 259617 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].[C:12]([O-])(=[O:14])[CH3:13].[Na+].[C:17]([NH:20][CH2:21][C:22]([OH:24])=[O:23])(=O)[CH3:18].C(OC(=O)C)(=O)C>>[CH3:18][C:17]1[O:24][C:22](=[O:23])[C:21](=[CH:6][C:5]2[CH:8]=[CH:9][C:2]([O:1][C:12](=[O:14])[CH3:13])=[C:3]([O:10][CH3:11])[CH:4]=2)[N:20]=1

Participants

5

Reactant 4

HCID 1183VanillinHCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 517045Sodium Acetate

Product 1

HCID 27542985(4H)-Oxazolone, 4-[[4-(acetyloxy)-3-methoxyphenyl]methylene]-2-methyl-

Conditions

Temperature
0 °C

Procedure

152 g (1mol) of 4-hydroxy-3-methoxy-benzaldehyde, 41 g of sodium acetate, 80 g of N-acetylglycine and 242 g of acetic anhydride are heated together for 30 minutes to 100° C. and then for 21/2 hours to the refluxing temperature. The resulting solution is cooled to 0° C. and the crystals which have separated out are filtered off and washed with water. The crude 2-methyl-4-(3-methoxy-4-acetoxy-benzylidene)-5(4H)-oxazolone thus obtained is heated to the boil with 1,400 ml of acetone and 545 ml of water for 15 hours under a reflux condenser. Thereafter, the acetone is largely distilled off, whereupon the product crystallises out. After filtration, and washing with acetone, 4-acetoxy-α-acetylamino-3-methoxycinnamic acid of melting point 205°-206° C. is obtained.

Workup

  1. custom2 hours
  2. customthe crystals which have separated out
  3. filtrationare filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-320f9b6658b2486faea4de9be3a5b2f0
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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