Potassium Hydroxide → 3-(4-i-Butylphenylthio)-4-ketocyclohexane acetic acid ethyl ester

HRID 1156166노트

반응식

HRID 1156166 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[K+].[CH2:14]([O:16][C:17](=[O:27])[CH2:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH:21](Br)[CH2:20]1)[CH3:15]>C(O)C>[CH2:14]([O:16][C:17](=[O:27])[CH2:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH:21]([S:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=2)[CH2:20]1)[CH3:15]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 130650933-Bromo-4-ketocyclohexaneacetic acid ethyl esterHCID 234667804-(2-Methylpropyl)benzene-1-thiol

생성물 1

HCID 130651303-(4-i-Butylphenylthio)-4-ketocyclohexane acetic acid ethyl ester

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

31.4 G. of 4-i-butylthiophenol and a solution of 10.6 g. of 85% potassium hydroxide in 300 ml. of ethanol were each placed in a 3 liter three-necked flask, provided with a condenser, nitrogen inlet, dropping funnel and stirrer. The solution was brought to reflux and a solution of 49.5 g. of 3-bromo-4-ketocyclohexaneacetic acid ethyl ester in 500 ml. of ethanol was added over a period of one hour to the refluxing solution. After the addition, the solution was stirred at reflux for one hour, cooled to room temperature, and filtered to remove the potassium bromide. After removal of the ethanol in vacuo (steam bath, rotary evaporator), 300 ml. of water was added to the residue, the product was extracted three times with 200 ml. of ether and the ether extract dried over anhydrous magnesium sulfate. After removal of ether from a steam bath at atmospheric pressure, the residue was distilled in vacuo. A yield of 42.5 g. of 3-(4-i-butylphenylthio)-4-ketocyclohexane acetic acid ethyl ester was obtained, b.p. 205-220/2.0 mm.

후처리

  1. customeach placed in a 3 liter three-necked flask
  2. customprovided with a condenser, nitrogen inlet
  3. temperatureto reflux
  4. additionAfter the addition
  5. temperatureat reflux for one hour
  6. filtrationfiltered
  7. customto remove the potassium bromide
  8. customAfter removal of the ethanol
  9. customin vacuo (steam bath, rotary evaporator), 300 ml
  10. additionof water was added to the residue
  11. extractionthe product was extracted three times with 200 ml
  12. extractionof ether and the ether extract
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customAfter removal of ether from a steam bath at atmospheric pressure
  15. distillationthe residue was distilled in vacuo

출처 및 근거

ORD 기록
ord-683c09347e9d454eb86ad97150a33615
출처 데이터셋
uspto-grants-1982_06
특허 번호
US04334078

반응 노트

불러오는 중…