Toluene → HCID 20335297, compound

HRID 1447779Notes

Reaction equation

HRID 1447779 reaction equation
C1(C)C=CC=CC=1.[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:22]([CH2:24][C:25]([O:27][CH2:28][CH2:29][O:30][C:31](=[O:33])[CH3:32])=[O:26])#[N:23].C([O-])(=O)C.[NH4+]>O.C(O)(=O)C>[C:22]([C:24](=[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:25]([O:27][CH2:28][CH2:29][O:30][C:31](=[O:33])[CH3:32])=[O:26])#[N:23]

Participants

7

Reactant 4

HCID 1140TolueneHCID 3102BenzophenoneHCID 517165Ammonium AcetateHCID 20227808HCID 20227808, compound

Product 1

HCID 20335297HCID 20335297, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A three-neck round bottom flask fitted with a mechanical stirrer, a thermometer and a Dean-Stark trap fitted with a reflux condenser was charged with 200 ml. of toluene, 182 g. (1 mole) of benzophenone, 205 g. (1.2 moles) of 2-acetoxyethyl 2-cyanoacetate, 40 ml. of glacial acetic acid, 16 g. of ammonium acetate. The contents were heated to reflux (110° C.) for 24 hours while the theoretical amount of water by-product was removed by azeotropic distillation. Upon removal of the solvent, as well as unreacted starting material by vacuum distillation, a yield of 200 g. (60%) of the desired product was obtained.

Workup

  1. customA three-neck round bottom flask fitted with a mechanical stirrer
  2. customa thermometer and a Dean-Stark trap fitted with a reflux condenser
  3. additionwas charged with 200 ml
  4. temperatureThe contents were heated
  5. customwas removed by azeotropic distillation
  6. customUpon removal of the solvent
  7. distillationby vacuum distillation

Sources & evidence

ORD record
ord-3c6beeb4de2d4f69824a8b664f737f5d
Source dataset
uspto-grants-1979_12
Patent number
US04178303

Reaction notes

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