Acetic Anhydride → HCID 54158325, compound

HRID 436425Notes

Reaction equation

HRID 436425 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]=O)=[CH:18][CH:19]=1.C(OC(=O)C)(=O)C>C1(C)C(C)=CC=CC=1>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[CH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 312444-MethoxybenzaldehydeHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 54158325HCID 54158325, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The starting material was prepared by refluxing for 72 hours a mixture of methyl 6-methylnicotinate (60.4 g.), anisaldehyde (163.3 g.), acetic anhydride (120 ml.) and xylene (320 ml.). Steam distillation was used to remove the excess anisaldehyde, the acetic acid formed during the reaction and xylene. The residue was dried in the cold, washed with ether, and dried at 60° C. for 12 hours to give methyl 6-p-methoxystyrylnicotinate, m.p. 170° C.

Workup

  1. customThe starting material was prepared
  2. temperatureby refluxing for 72 hours
  3. distillationSteam distillation
  4. customto remove the excess anisaldehyde
  5. customthe acetic acid formed during the reaction and xylene
  6. customThe residue was dried in the cold
  7. washwashed with ether
  8. customdried at 60° C. for 12 hours

Sources & evidence

ORD record
ord-2969d96651b44c818b1010ceb8cd5d48
Source dataset
uspto-grants-1977_02
Patent number
US04009174

Reaction notes

Loading…