Acetic Acid → 5,6-Methylenedioxy-2-nitro-3-phenylbenzofuran

HRID 46625

반응식

HRID 46625 반응식
Br[C:2]1[O:3][C:4]2[CH:16]=[C:15]3[O:17][CH2:18][O:19][C:14]3=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)C.C1CCC(C(O)=O)CC=1.[N+:33]([O-:38])([N+]([O-])=O)=[O:34]>O>[CH2:18]1[O:17][C:15]2=[CH:16][C:4]3[O:3][C:2]([N+:33]([O-:38])=[O:34])=[C:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=3[CH:13]=[C:14]2[O:19]1

참가 물질

6

반응물 4

HCID 176Acetic Acid2회HCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 544242002-Bromo-5,6-methylenedioxy-3-phenylbenzofuran

생성물 1

HCID 541688035,6-Methylenedioxy-2-nitro-3-phenylbenzofuran

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 5.2 g. (0.016 mole) of 2-bromo-5,6-methylenedioxy-3-phenylbenzofuran in 225 ml. of acetic acid is added with stirring 5.0 g. (0.024 mole) of cyclohexene-4-carboxylic acid, then 2.2 g. (0.024 mole) of dinitrogen tetraoxide in 25 ml. of acetic acid. After about one hour the mixture is poured into cold water, and the yellow product is collected and washed with water. The product is dissolved in dichloromethane, and the solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution, then dried. The solution is concentrated to dryness to provide a yellow residue which is recrystallized from a benzene-hexane mixture, then from an isopropanol-benzene mixture to provide yellow needles of 5,6-methylenedioxy-2-nitro-3-phenylbenzofuran, m.p. 180°-183° C.

후처리

  1. customthe yellow product is collected
  2. washwashed with water
  3. dissolutionThe product is dissolved in dichloromethane
  4. washthe solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution
  5. customdried
  6. concentrationThe solution is concentrated to dryness
  7. customto provide a yellow residue which
  8. customis recrystallized from a benzene-hexane mixture

출처 및 근거

ORD 기록
ord-a38d89104c9f443cab73e1460278556b
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04174403

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