Dimethyl Sulfoxide → 2,6-Dichloro-4-nitrobenzaldehyde

HRID 746040

反応式

HRID 746040 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:13]=1[CH2:14][OH:15].C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:13]=1[CH:14]=[O:15]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23311409(2,6-Dichloro-4-nitrophenyl)methanol

生成物 1

HCID 218388352,6-Dichloro-4-nitrobenzaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of dimethyl sulphoxide (1.2 cm3) in dichloromethane (5 cm3) was added dropwise to a stirred solution of oxalyl chloride (0.7 cm3, 8.0 mmol) in dichloromethane (12 cm3) at -60° C. under nitrogen. After 10 mins at -60° C. a solution of 2,6-dichloro-4-nitrobenzylalcohol (1.53 g, 6.9 mmol) in dichloromethane (10 cm3) was added dropwise and the stirred mixture kept at -60° C. for 0.5 h. Triethylamine (4.6 cm3, 33 mmol) was then added and the mixture was allowed to warm to room temperature at which stage water (35 cm3) was added. The heterogeneous mixture was separated and the aqueous phase extracted with dichloromethane (35 cm3). The combined organic fractions were extracted with hydrochloric acid (2M, 60 cm3), then water (60 cm3), saturated sodium carbonate solution (60 cm 3), and finally water (60 cm3) then dried and evaporated under reduced pressure to give 2,6-dichloro-4-nitrobenzaldehyde as a pure oil which slowly solidified.

後処理

  1. additionwas added
  2. customThe heterogeneous mixture was separated
  3. extractionthe aqueous phase extracted with dichloromethane (35 cm3)
  4. extractionThe combined organic fractions were extracted with hydrochloric acid (2M, 60 cm3)
  5. dry with materialwater (60 cm3), saturated sodium carbonate solution (60 cm 3), and finally water (60 cm3) then dried
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-5c34ea4784db4b95bab3b91e2d6a1307
出典データセット
uspto-grants-1986_07
特許番号
US04602041

関連ノート

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