Triethylamine → 3-Chloro-4-methylbenzaldehyde

HRID 1828810Notes

Reaction equation

HRID 1828810 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 dimethyl sulfoxide (10 ml) was added sulfur trioxide-pyridine complex (4.47 g) under water-cooling. The mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into ice water and the mixture was extracted with diethyl ether. The organic layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution and dried over magnesium sulfate. The residue was concentrated to dryness under reduced pressure to give 3-chloro-4-methylbenzaldehyde (1.40 g) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe residue was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b5a2960a123b493a8fb714cc1bd8e9f4
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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