Triethylamine → 3-Chloro-4-methylbenzaldehyde

HRID 1699938Notes

Reaction equation

HRID 1699938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH2:5][OH:6].C(N(CC)CC)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 1234863-Chloro-4-methylbenzyl alcohol

Product 1

HCID 124230853-Chloro-4-methylbenzaldehydeYield 70.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-chloro-4-methylbenzyl alcohol (2.00 g) and triethylamine (8.9 ml) in a dimethyl sulfoxide (10 ml) was added sulfur trioxide-pyridine complex (4.47 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into ice water, and extracted with ether. The organic layer was washed with 1N hydrochloric acid, saturated brine and a saturated aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate, and concentrated to dryness under reduced pressure to give the objective compound (1.40 g) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. extractionextracted with ether
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated brine
  4. dry with materiala saturated aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-43542edb0be543ddbd5a8cfa038b831f
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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