1,2-Dichloroethane → 2-Methyl-4-(1-oxopropoxy)-2-butenal

HRID 21850

반응식

HRID 21850 반응식
[C:1]([O:5][CH2:6][CH:7]=[C:8]([CH3:11])[CH2:9]Cl)(=[O:4])[CH2:2][CH3:3].C1N2CN3CN(C2)CN1C3.C1N2S(=O)(=O)N3CN(C2)S(=O)(=[O:29])N1C3.ClCCCl>O>[C:1]([O:5][CH2:6][CH:7]=[C:8]([CH3:11])[CH:9]=[O:29])(=[O:4])[CH2:2][CH3:3]

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 4101HexamethylenetetramineHCID 64148TetramethylenedisulfotetramineHCID 536568944-Propionyloxy-2-methyl-1-chloro-2-butene2회

생성물 1

HCID 572397522-Methyl-4-(1-oxopropoxy)-2-butenal수율 26.8%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
35 °C

실험 절차

The crude 4-propionyloxy-2-methyl-1-chloro-2-butene (64.0 g, 0.362 mol) obtained in the above (i) was added to a solution of hexamethylenetetramine (50.9 g, 0.363 mol) in water (345 ml), and the mixture was stirred at 35° C. for 4 hours to prepare a tetramine salt. 1,2-Dichloroethane (200 ml) was added to the reaction mixture, and compounds insoluble in water were removed by extraction. 1,2-Dichloroethane (400 ml) was further added to the aqueous layer that had been washed, and the mixture was stirred at 60° C. for 4 hours to hydrolyze the tetramine salt. After completion of the reaction, the 1,2-dichloroethane layer was separated, and 1,2-dichloroethane (250 ml) was further added to the aqueous layer for extraction. The 1,2-dichloroethane layers were combined and dried over anhydrous sodium sulfate. The 1,2-dichloroethane was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane (=1:5)) to give 4-propionyloxy-2-methyl-2-buten-1-al (15.2 g, 0.0973 mol, Yield: 26.8% ).

후처리

  1. customwere removed by extraction
  2. addition1,2-Dichloroethane (400 ml) was further added to the aqueous layer that
  3. washhad been washed
  4. stirringthe mixture was stirred at 60° C. for 4 hours
  5. customAfter completion of the reaction
  6. customthe 1,2-dichloroethane layer was separated
  7. addition1,2-dichloroethane (250 ml) was further added to the aqueous layer for extraction
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe 1,2-dichloroethane was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane (=1:5))

출처 및 근거

ORD 기록
ord-058f1754f95a4ac2af5d634a51172185
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424478

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