Triethylamine → 3-Chloro-4-methylbenzaldehyde

HRID 1072918Notes

Reaction equation

HRID 1072918 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-b4620fcd7c954d86942a6dccf0e9c7d1
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

Loading…