Hydrochloric Acid → 1-(2-Nitro-3-phenyl-5-benzofuranyl)undecan-1-ol

HRID 262218

반응식

HRID 262218 반응식
[OH:1][CH:2]([C:13]1[CH:14]=[CH:15][C:16]2[O:20][CH:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]=2[CH:27]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N+:28]([O-:33])([N+]([O-])=O)=[O:29].[OH-].[Na+].Cl>ClCCl.C(OCC)C>[N+:28]([C:19]1[O:20][C:16]2[CH:15]=[CH:14][C:13]([CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:27][C:17]=2[C:18]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O-:33])=[O:29]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25352Nitrogen oxide (N2O4)HCID 213202985-(alpha-Hydroxyundecyl)-3-phenylbenzofuran

생성물 1

HCID 213202791-(2-Nitro-3-phenyl-5-benzofuranyl)undecan-1-ol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To the solution of product from step A is added 2 g. of dinitrogen tetraoxide dissolved in dichloromethane, and the mixture is stirred for about 16 hours. Evaporation provides a residue which is mixed with ice and 10 percent sodium hydroxide solution. The mixture is stirred for 15 minutes, then cold 6N hydrochloric acid and diethyl ether are added. The ether layer is separated, then washed with saturated sodium chloride solution and dried. The solution is chromatographed on silica gel, eluting first with carbon tetrachloride, then dichloromethane. The later fractions are evaporated to provide 1-(2-nitro-3-phenyl-5-benzofuranyl)undecan-1-ol as a yellow solid, m.p. 84°-85° C. after recrystallization from hexane.

후처리

  1. customEvaporation
  2. customprovides a residue which
  3. stirringThe mixture is stirred for 15 minutes
  4. customThe ether layer is separated
  5. washwashed with saturated sodium chloride solution
  6. customdried
  7. customThe solution is chromatographed on silica gel
  8. washeluting first with carbon tetrachloride
  9. customThe later fractions are evaporated

출처 및 근거

ORD 기록
ord-9f6ed11aec8d491eb62d5fa6a407c1be
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04153716

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