Hydrochloric Acid → 1-(4-Bromophenyl)-2-nitro-1,3-diacetoxypropane

HRID 2417628노트

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HRID 2417628 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[N+:10]([CH:13](O)[CH3:14])([O-:12])=[O:11].Cl.[C:17]([O:20]C(=O)C)(=[O:19])[CH3:18].[C:24](Cl)(=[O:26])[CH3:25]>CCOCC.O.C(N(CC)CC)C.CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([O:7][C:24](=[O:26])[CH3:25])[CH:13]([N+:10]([O-:12])=[O:11])[CH2:14][O:20][C:17](=[O:19])[CH3:18])=[CH:4][CH:3]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 707414-BromobenzaldehydeHCID 22056827Nitroethanol

생성물 1

HCID 134688951-(4-Bromophenyl)-2-nitro-1,3-diacetoxypropane수율 79%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8471Triethylamine용매

반응 조건

온도
-3 °C

실험 절차

A mixture of 18.5 g (0.1 moles) of p-bromobenzaldehyde, 20 ml of methanol and 0.5 ml of triethylamine is cooled to -3° C., and 9.1 g (0.1 moles) of nitroethanol are added within one hour. The reaction mixture is stirred for 4 hours at 0°-5° C. 50 ml of water are added to the mixture, the mixture is cooled to 5° C., 30 ml of 0.5 n hydrochloric acid are added, and the mixture is stirred for 10 minutes. Thereafter 30 ml of ether are added to the mixture, the phases are separated from each other, and the etheral phase is evaporated. 30 g (0.29 moles) of acetic anhydride and 2 ml of acetyl chloride are added to the residue, the mixture is stirred at 60° C. for 2 hours, thereafter it is poured onto 100 g of ice and stirred for 3 hours. The separated product is filtered off. 28.7 g (79%) of the title compound are obtained; m.p.: 81°-82° C. According to thin layer chromatography the product is uniform; Rf =0.76 (solvent: a 90:10:1 mixture of benzene, methanol and acetone).

후처리

  1. temperaturethe mixture is cooled to 5° C.
  2. stirringthe mixture is stirred for 10 minutes
  3. customthe phases are separated from each other, and the etheral phase
  4. customis evaporated
  5. stirringthe mixture is stirred at 60° C. for 2 hours
  6. stirringstirred for 3 hours
  7. filtrationThe separated product is filtered off

출처 및 근거

ORD 기록
ord-0da6b10105f84786b8bd67bb8b7b2126
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04469703

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