Toluene → HCID 54309886, compound

HRID 638227Notes

Reaction equation

HRID 638227 reaction equation
C(O[CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)C.[C:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18].C([O-])(=O)C.[NH4+].C1(C)C=CC=CC=1>O>[C:17]([C:19](=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 6009134-Propylbenzaldehyde diethyl acetal

Product 1

HCID 54309886HCID 54309886, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20.0 g (90 mmole) 4-n-propylbenzaldehyde diethylacetal, 20.4 g (180 mmole) ethyl cyanoacetate, 7.2 g (93.4 mmole) ammonium acetate and 60 ml toluene are heated at reflux for six hours, cooled and poured into water. The resulting mixture was extracted with ethyl ether, dried (MgSO4) and the volatiles evaporated in vacuo to afford 23.0 g crude yellow oil which was purified by chromatography on a silica gel column, eluting with 2:1 methylene chloride/hexane to give 20.58 g (94%) of the desired product. 1H-NMR(CDCl3)ppm(delta): 0.85-1.95 (m, 8H), 2.45-2.70 (t, 2H), 4.15-4.60 (q, 2H), 7.15-8.05 (q, 4H), 8.25 (s, 1H).

Workup

  1. temperatureare heated
  2. temperatureat reflux for six hours
  3. temperaturecooled
  4. extractionThe resulting mixture was extracted with ethyl ether
  5. dry with materialdried (MgSO4)
  6. customthe volatiles evaporated in vacuo
  7. customto afford 23.0 g crude yellow oil which
  8. customwas purified by chromatography on a silica gel column
  9. washeluting with 2:1 methylene chloride/hexane

Sources & evidence

ORD record
ord-7e6f9e401d1241ada707af4ebd3ef4e9
Source dataset
uspto-grants-1985_12
Patent number
US04560690

Reaction notes

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