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

HRID 746040

반응식

HRID 746040 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 218388352,6-Dichloro-4-nitrobenzaldehyde

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c34ea4784db4b95bab3b91e2d6a1307
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04602041

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