Hydrochloric Acid → HCID 54226950, compound

HRID 1077407Notes

Reaction equation

HRID 1077407 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH:19]=O.Cl.[OH-].[Na+]>O.C(O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH:19]=[C:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8419VeratraldehydeHCID 141126-Methoxy-alpha-tetraloneHCID 14798Sodium Hydroxide

Product 1

HCID 54226950HCID 54226950, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6-Methoxy-1-tetralone (7.04 g, 40 mmol) and 3,4-dimethoxybenzaldehyde (6.44 g, 40 mmol) are mixed with 100 ml of absolute ethanol. The mixture is stirred for 0.5 h to dissolve as much as possible of the reagents. The introduction of gaseous hydrogen chloride is commenced. An exothermic reaction is noted which enables the complete dissolution of all of the reagents. The round-bottomed flask is cooled from time to time with an ice bath so that the temperature does not exceed 80° C. The mixture is thus saturated with hydrogen chloride after 1 h to give an intense red color. This mixture is allowed to stand at room temperature for 2 h. The reaction mixture is poured into a mixture of 400 ml of water and 40 ml of aqueous NaOH (3N). It is stirred vigorously for 3 h at room temperature. The precipitated solid is filtered over a glass frit, washed with water and finally dried under vacuum, over P2O5, to give a solid (12.35 g, 95%). A small quantity of product is recrystallized from the mixture AcOEt/hexane=1:2.

Workup

  1. dissolutionto dissolve as much as possible of the reagents
  2. customAn exothermic reaction
  3. dissolutionthe complete dissolution of all of the reagents
  4. temperatureThe round-bottomed flask is cooled from time to time with an ice bath so that the temperature
  5. customdoes not exceed 80° C
  6. customto give an intense red color
  7. waitto stand at room temperature for 2 h
  8. stirringIt is stirred vigorously for 3 h at room temperature
  9. filtrationThe precipitated solid is filtered over a glass frit
  10. washwashed with water
  11. dry with materialfinally dried under vacuum, over P2O5

Sources & evidence

ORD record
ord-21ac01bde77a4496950c8a2251c6871b
Source dataset
uspto-grants-1996_08
Patent number
US05543298

Reaction notes

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