1,2,3-Trimethylbenzene → 2,3,4-trimethylbenzaldehyde

HRID 361295Notes

Reaction equation

HRID 361295 reaction equation
Cl[Sn](Cl)(Cl)Cl.ClC([O:9][CH3:10])Cl.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[CH3:19]>ClCCl>[CH3:11][C:12]1[C:13]([CH3:19])=[C:14]([CH3:18])[CH:15]=[CH:16][C:17]=1[CH:10]=[O:9]

Participants

5

Reactant 3

HCID 106861,2,3-TrimethylbenzeneHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachloride

Product 1

HCID 27525972,3,4-trimethylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

To a stirred solution of SnCl4 (39 g, 0.15 mol) in 50 mL of dichloromethane was added dropwise at -5° C. a solution of 15 g (0.13 mol) of dichloromethylmethylether. This solution was stirred at -5° C. for one hour before adding dropwise over 10 min a solution of 12 g (0.1 mol) of 1,2,3-trimethylbenzene. The mixture was stirred at 0° C. for 15 min before warming to room temperature where it was stirred an additional 1.5 hrs. After quenching onto 100 g of ice the organic layer was separated, washed with water, saturated aqueous sodium bicarbonate and water before drying over Na2SO4, filtering and evaporating to dryness in vacuo. The product was purified by distillation in vacuo. B.p. 120°-122° C. (11 mm). Lit. b.p. 121.5 (11 mm) Yield: 9.2 g (70%).

Workup

  1. stirringThe mixture was stirred at 0° C. for 15 min
  2. temperaturebefore warming to room temperature where it
  3. stirringwas stirred an additional 1.5 hrs
  4. customAfter quenching onto 100 g of ice the organic layer
  5. customwas separated
  6. washwashed with water, saturated aqueous sodium bicarbonate and water
  7. dry with materialbefore drying over Na2SO4
  8. filtrationfiltering
  9. customevaporating to dryness in vacuo
  10. distillationThe product was purified by distillation in vacuo

Sources & evidence

ORD record
ord-33a27399976e435da7c4122130599136
Source dataset
uspto-grants-1999_02
Patent number
US05866513

Reaction notes

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