Acetic Acid → HCID 54267703, compound

HRID 1065788Notes

Reaction equation

HRID 1065788 reaction equation
C([C:7]1[N:11]=[CH:10][NH:9][N:8]=1)(C(C)(C)C)C.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH:22]=O.N1CCCCC1.[C:30]([OH:33])(=O)[CH3:31].[C:34]1([CH3:40])[CH:39]=CC=C[CH:35]=1>CCOCC.O>[CH3:35][C:34]([CH3:40])([CH3:39])[C:30](=[O:33])[C:31]([N:8]1[CH:7]=[N:11][CH:10]=[N:9]1)=[CH:22][C:13]1[CH:14]=[CH:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 1140TolueneHCID 62012-NaphthalenecarboxaldehydeHCID 8082PiperidineHCID 178437749HCID 178437749, compound

Product 1

HCID 54267703HCID 54267703, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

16.7 g (0.1 mole) of pinacolyl-1,2,4-triazole, 15.6 g (0.1 mole) of 2-naphthaldehyde, 1 g of piperidine and 3 g of glacial acetic acid in 50 ml of toluene were heated under reflux, using a water separator, until no further water passed over. After cooling the reaction solution, it was diluted by adding ether and washed with water. The organic phase was dried over sodium sulphate and concentrated by distilling off the solvents in vacuo. The residue was distilled in vacuo. 18 g (59% of theory) of 4,4-dimethyl-1-(naphth-2-yl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one of boiling point 220° C. were obtained.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling the reaction solution, it
  3. additionwas diluted
  4. washwashed with water
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvents in vacuo
  8. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-335462cc28c641dab9603e2fad65464b
Source dataset
uspto-grants-1982_05
Patent number
US04331675

Reaction notes

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