Acetic Acid → 1(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-

HRID 1982284Notes

Reaction equation

HRID 1982284 reaction equation
C(OC(=O)C)(=O)C.C(O)(=O)C.[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[CH3:23][N:24]([CH3:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29]>CO>[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[C:31]3[C:27](=[CH:26][C:25]([N:24]([CH3:34])[CH3:23])=[CH:33][CH:32]=3)[C:28](=[O:29])[O:19]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 7918Acetic AnhydrideHCID 668373-(Dimethylamino)benzoic acid

Product 1

HCID 936931(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-Yield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A stirred mixture of 306.0 g of acetic anhydride, 200.0 ml of glacial acetic acid, 298.0 g p-dimethylaminobenzaldehyde and 386.0 g of m-dimethylaminobenzoic acid was heated at reflux for a period of approximately four hours. The resulting mixture was cooled to 55° C., diluted with 700 ml of methanol and heated at reflux for approximately thirty minutes. The mixture was then cooled to approximately 15° C. and the solid which separated was collected by filtration and washed with 700.0 ml of fresh methanol chilled to 10°-15° C. The methanol-wet solid was reslurried in 400 ml of fresh methanol at 10°-15° C. for approximately twenty minutes, separated by filtration and washed with 150 ml of chilled methanol. The solid was dried at 70° C. in vacuo to yield 453.2 g of 3-(4-dimethylaminophenyl)-6-dimethylaminophthalide (Formula II: R=CH3 ; X=H; Y=4-(CH3)2N--C6H4 which after recrystallization from toluene was obtained as an ivory-colored solid melting at 184.5°-185.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for a period of approximately four hours
  3. temperatureheated
  4. temperatureat reflux for approximately thirty minutes
  5. temperatureThe mixture was then cooled to approximately 15° C.
  6. customthe solid which separated
  7. filtrationwas collected by filtration
  8. washwashed with 700.0 ml of fresh methanol
  9. temperaturechilled to 10°-15° C
  10. waitThe methanol-wet solid was reslurried in 400 ml of fresh methanol at 10°-15° C. for approximately twenty minutes
  11. customseparated by filtration
  12. washwashed with 150 ml of chilled methanol
  13. customThe solid was dried at 70° C. in vacuo

Sources & evidence

ORD record
ord-225a0dc12e254bcaafa3f7444922125d
Source dataset
uspto-grants-1986_06
Patent number
US04595768

Reaction notes

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