Hydrochloric Acid → 1-Thiophen-2-yldodecan-1-one

HRID 1196800노트

반응식

HRID 1196800 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6](Cl)(=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].Cl[Sn](Cl)(Cl)Cl.Cl>C1C=CC=CC=1>[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8030ThiopheneHCID 8166Dodecanoyl chlorideHCID 24287Tin tetrachloride

생성물 1

HCID 35880811-Thiophen-2-yldodecan-1-one수율 75.7%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

In a 5 liter-five-necked flask, 112.5 g (1.34 mol) of thiophene, 300 g (1.37 mol) of n-dodecanoyl chloride and 2.25 liter of dry benzene were placed and cooled below 0° C. To the mixture under stirring, 148.5 (5.70×10-1 mole) of SnCl4 was added dropwise in 1 hour below 0° C. The mixture was stirred for 30 min. below 0° C., followed by stirring for 4 hours while being gradually restored to room temperature. After the reaction, 2 liter of 10% HCl was added to the reaction mixture, followed by stirring for 10 min. The separated organic layer was successively washed three times with 500 ml each of 10% HCl, water, 5% Na2CO3 and water, followed by drying with CaCl2 and distilling-off of the solvent to obtain 315 g of a crude product. The crude product was subjected to reduced-pressure distillation under an atmosphere of nitrogen to obtain 270 g of a pure product (yield: 75.7%). b.p.: 146° C./0.65 mmHg

후처리

  1. temperaturecooled below 0° C
  2. stirringThe mixture was stirred for 30 min. below 0° C.
  3. stirringby stirring for 4 hours
  4. customwhile being gradually restored to room temperature
  5. additionwas added to the reaction mixture
  6. stirringby stirring for 10 min
  7. washThe separated organic layer was successively washed three times with 500 ml each of 10% HCl, water, 5% Na2CO3 and water
  8. dry with materialby drying with CaCl2 and distilling-off of the solvent
  9. customto obtain 315 g of a crude product
  10. distillationThe crude product was subjected to reduced-pressure distillation under an atmosphere of nitrogen

출처 및 근거

ORD 기록
ord-549ddf7856c74e7a85b67ff233e39423
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05116530

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