Acetic Anhydride → 2-Methyl-4-(4-acetoxy-3-allyl-benzylidene)-5(4H)-oxazolone

HRID 597652Notes

Reaction equation

HRID 597652 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=O)[CH:2]=[CH2:3].[C:13]([O-])(=[O:15])[CH3:14].[Na+].[C:18]([NH:21][CH2:22][C:23]([OH:25])=[O:24])(=O)[CH3:19].C(OC(=O)C)(=O)C>>[CH3:19][C:18]1[O:25][C:23](=[O:24])[C:22](=[CH:7][C:6]2[CH:9]=[CH:10][C:11]([O:12][C:13](=[O:15])[CH3:14])=[C:4]([CH2:1][CH:2]=[CH2:3])[CH:5]=2)[N:21]=1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 517045Sodium AcetateHCID 47290143-Allyl-4-hydroxybenzaldehyde

Product 1

HCID 536773552-Methyl-4-(4-acetoxy-3-allyl-benzylidene)-5(4H)-oxazolone

Conditions

Temperature
0 °C

Procedure

40.5 g (0.25 mol) of 3-allyl-4-hydroxy-benzaldehyde, 10.3 g of sodium acetate, 19.9 g of N-acetylglycine and 63.5 g of acetic anhydride are together heated for 30 minutes to 100°C and then for 21/2 hours to the reflux temperature. The resulting solution is cooled to 0°C and the crystals which have separated out are filtered off, washed with water, dried in a vacuum desiccator and finally recrystallised from carbon tetrachloride. 2-Methyl-4-(4-acetoxy-3-allyl-benzylidene)-5(4H)-oxazolone of melting point 108°-109°C is obtained.

Workup

  1. custom2 hours
  2. customthe crystals which have separated out
  3. filtrationare filtered off
  4. washwashed with water
  5. customdried in a vacuum desiccator
  6. customfinally recrystallised from carbon tetrachloride

Sources & evidence

ORD record
ord-97f9d10739114340918dadef831fe861
Source dataset
uspto-grants-1977_03
Patent number
US04014920

Reaction notes

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