Dimethyl Sulfoxide → 2-(2,4-Dichlorophenoxy)propanal

HRID 476844

反応式

HRID 476844 の反応式
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]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3509832-(2,4-Dichlorophenoxy)propan-1-ol

生成物 1

HCID 221663592-(2,4-Dichlorophenoxy)propanal収率 22.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-60 °C

実験手順

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.

後処理

  1. waitAfter a further 5 minutes at -60° C. the mixture was allowed
  2. temperatureto warm to room temperature
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with 150 ml of methylene chloride
  5. washthe combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel
  9. washfor the elution

出典と根拠

ORDレコード
ord-6bbe6b5ead9c42a59d208ecb2cb25c51
出典データセット
uspto-grants-1989_12
特許番号
US04886785

関連ノート

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