Carbon Tetrachloride → 1,3,5-Trichloro-2-(2-chloroethoxy)benzene

HRID 1535039

반응식

HRID 1535039 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:3]=1[O:4][CH2:5][CH2:6]O.C(Cl)(Cl)(Cl)[Cl:15].S(Cl)(Cl)=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:3]=1[O:4][CH2:5][CH2:6][Cl:15]

참가 물질

6

반응물 3

HCID 5943Carbon TetrachlorideHCID 24386Thionyl Chloride3회HCID 963432-(2,4,6-Trichlorophenoxy)ethan-1-ol

생성물 1

HCID 112769591,3,5-Trichloro-2-(2-chloroethoxy)benzene수율 98%

시약·촉매·용매 2

HCID 5963Benzyltrimethylammonium chloride촉매HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

Into a three-necked, round-bottom flask fitted with a stirrer, thermometer, reflux condenser and dropping funnel was added 250 g of 96% 2-(2,4,6-trichlorophenoxy) ethanol, 250 ml carbon tetrachloride and 4 g of benzyl-trimethyl-ammonium chloride. The mixture was heated to 55° C. and 146 g thionyl chloride was added dropwise over 1.5 hours. After the addition of the thionyl chloride the temperature of the reaction was slowly raised to 80° C. for a total reaction tme of 2.5 to 3 hours. The end of the reaction was determined by GLC. The mixture was cooled to 60° C. and water slowly added to decompose the excess thionyl chloride. The phases were separated and the organic phase was washed with a 10% sodium hydroxide solution until it reached a pH of 7. After an additional separation of the phases the organic phase was washed again with water. After a further separation of phases, the carbon tetrachloride was distilled off to yield an oil which slowly crystallized to form 257 g of 2-(2,4,6-trichlorophenoxy)-ethyl chloride in a purity of 96%-98% and yield of 98%.

후처리

  1. customInto a three-necked, round-bottom flask fitted with a stirrer
  2. temperaturethermometer, reflux condenser
  3. temperaturewas slowly raised to 80° C. for a total reaction tme of 2.5 to 3 hours
  4. temperatureThe mixture was cooled to 60° C.
  5. customThe phases were separated
  6. washthe organic phase was washed with a 10% sodium hydroxide solution until it
  7. customAfter an additional separation of the phases the organic phase
  8. washwas washed again with water
  9. customAfter a further separation of phases
  10. distillationthe carbon tetrachloride was distilled off
  11. customto yield an oil which
  12. customslowly crystallized

출처 및 근거

ORD 기록
ord-83e99dc639134bbfa83ebdc2cc54716a
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05091578

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