Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:13]=1[O:14][CH:15]([CH3:18])[CH2:16][OH:17].C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:13]=1[O:14][CH:15]([CH3:18])[CH:16]=[O:17]Participants
Conditions
- Temperature
- -60 °C
Procedure
4.68 g of DMSO were added under nitrogen to a stirred solution of 3.81 g of oxalyl chloride in 75 ml of methylene chloride at -60° C. to -50° C. After 2 minutes a solution of 6.4 g of 2-(2,4-dichlorophenoxy)propanol in 40 ml of methylene chloride was added. The mixture was stirred at -60° C. for a further 15 minutes and was then treated with 13.7 g of triethylamine After a further 5 minutes at -60° C. the mixture was allowed to warm to room temperature. 150 ml of water were added and the layers were separated. The aqueous layer was extracted with 150 ml of methylene chloride and the combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water, dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica gel using ethyl acetate/n-hexane (1:4) for the elution. There were obtained 1.4 g of 2-(2,4-dichlorophenoxy)propionaldehyde, mp 87°-88° C.
Workup
- temperatureto warm to room temperature
- customthe layers were separated
- extractionThe aqueous layer was extracted with 150 ml of methylene chloride
- washthe combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water
- dry with materialdried over sodium sulphate
- customevaporated
- customThe residue was purified by chromatography on silica gel
- washfor the elution
Sources & evidence
- ORD record
- ord-77081c33126346a896356205fcf11eb7
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04956346
Linked notes
Loading…