Hydrochloric Acid → 2,4,6-Trimethylbenzaldehyde

HRID 651959Notes

Reaction equation

HRID 651959 reaction equation
[C:1]1([CH3:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].ClS(O)(=O)=O.[C]=O.Cl.[C:22](OCC)(=[O:24])C>[Ni](Cl)Cl.O.C1C=CC=CC=1.C(O)=O>[CH3:9][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH:22]=[O:24]

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 7947MesityleneHCID 8857Ethyl AcetateHCID 24638Chlorosulfonic acidHCID 6451240Aluminum(III) ChlorideHCID 178418416HCID 178418416, compound

Product 1

HCID 102542,4,6-Trimethylbenzaldehyde

Reagents, catalysts & solvents 4

HCID 24385Nickel DichlorideCatalystHCID 241BenzeneSolvent2×HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A benzene solution of 180 g (1.5 moles) of mesitylene, 90 g of aluminum chloride and 13 g of nickel dichloride was stirred at 70° C. to 80° C. Simultaneously, 125 ml of formic acid was added dropwise to 230 ml of chlorosulfonic acid to generate carbon monoxide and hydrogen chloride gas which were blown into the above benzene solution for 6 hours. Next, water and ethyl acetate were added to the solution which was separated into an organic and an aqueous layer. The organic layer was washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/1) to give 34.5 g (0.233 mole) of 2,4,6-trimethylbenzaldehyde as a colorless oil.

Workup

  1. customwas separated into an organic and an aqueous layer
  2. washThe organic layer was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-6e8d6e09c87c4b46b130dc061902d36b
Source dataset
uspto-grants-1987_06
Patent number
US04670373

Reaction notes

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