Hydrochloric Acid → Benzaldehyde, 4,6-dihydroxy-2,3-dimethyl-

HRID 1110416Notes

Reaction equation

HRID 1110416 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[OH:10].OS(O)(=O)=O.[O-][Mn](=O)(=O)=O.[K+].[OH-].[Na+].Cl.[CH2:25]([O:27]CC)C>[C-]#N.[Zn+2].[C-]#N>[OH:9][C:5]1[CH:4]=[C:3]([OH:10])[C:2]([CH3:1])=[C:7]([CH3:8])[C:6]=1[CH:25]=[O:27]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 106974-MethylorcinolHCID 14798Sodium HydroxideHCID 516875Potassium Permanganate

Product 1

HCID 254155Benzaldehyde, 4,6-dihydroxy-2,3-dimethyl-

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

4.450 g (32 mmol) of 2,3-dimethyl-5-hydroxyphenol are dissolved in 100 ml of anhydrous ethyl ether in a round-bottomed flask equipped with a gas inlet, a thermometer and a condenser (the outflow gases being trapped by 3 successive bubblers: H2SO4, saturated KMnO4 solution, 3N NaOH). After 5.635 g (48 mmol) of zinc cyanide have been added, a stream of gaseous hydrochloric acid is passed through for 2 hours with stirring at room temperature. A copious precipitate appears, increasing with the passage of time. At the end of the operation, a powerful stream of nitrogen is passed through the reaction medium. The insoluble matter is separated by filtration and dissolved in boiling water. After cooling, the aldehyde precipitates. After filtration, the crystals are washed with water and dried.

Workup

  1. customequipped with a gas inlet
  2. customis passed through for 2 hours
  3. temperatureincreasing with the passage of time
  4. customThe insoluble matter is separated by filtration
  5. dissolutiondissolved
  6. temperatureAfter cooling
  7. customthe aldehyde precipitates
  8. filtrationAfter filtration
  9. washthe crystals are washed with water
  10. customdried

Sources & evidence

ORD record
ord-3ed6ddd7045b4f858a1bbc113bceab8b
Source dataset
uspto-grants-1990_12
Patent number
US04975455

Reaction notes

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