Ammonium Chloride → 6-Ethyl-4'-(1-ethyl-1-hydroxypropyl)-2'-propylbiphenyl-3-ol

HRID 1869727

반응식

HRID 1869727 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH2:20][CH2:21][CH3:22])[CH3:2].[CH2:23]([Mg]Br)[CH3:24].[Cl-].[NH4+]>O1CCCC1.C(OCC)C.O>[CH2:1]([C:3]1[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH2:23][CH3:24])([OH:19])[CH2:17][CH3:18])=[CH:12][C:11]=2[CH2:20][CH2:21][CH3:22])=[CH:5][C:6]([OH:9])=[CH:7][CH:8]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 223456391-(2'-Ethyl-5'-hydroxy-2-propylbiphenyl-4-yl)-1-propanoneHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 117168456-Ethyl-4'-(1-ethyl-1-hydroxypropyl)-2'-propylbiphenyl-3-ol수율 64%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

370 g (1.248 mol) of 1-(2′-ethyl-5′-hydroxy-2-propylbiphenyl-4-yl)propan-1-one in solution in 3.7 liters of tetrahydrofuran are placed in a reactor. 915 ml of a 3M solution of ethylmagnesium bromide in ethyl ether are slowly run into this solution cooled to −10° C. At the end of the addition, the reaction mixture is kept stirred for 1 hour and then transferred onto 5 liters of a 2.5 molar solution of ammonium chloride in water. The organic phase is separated by settling and washed twice with 800 ml of water. After evaporating under reduced vacuum, the residue is dissolved with 2.75 liters of methylene chloride at reflux. The medium is allowed to return to ambient temperature with stirring and is then cooled to 5° C. The crystals are filtered off and then dried under vacuum. 260 g (64%) of 6-ethyl-4′-(1-ethyl-1-hydroxypropyl)-2′-propylbiphenyl-3-ol are obtained. Melting point: 130° C. 1H NMR (d6-DMSO) (ppm): 0.67-0.74, m, 9H; 0.9, t, 3H; 1.38, m, 2H; 1.71-1.77, m, 4H; 2.13-2.35, m, 4H; 4.48, s, 1H; 6.45, d, 1H; 6.70, dd, 1H; 6.94, d, 1H; 7.07, d, 1H; 7.18, dd, 1H; 7.26, s, 1H; 9.16, s, 1H

후처리

  1. additionAt the end of the addition
  2. customThe organic phase is separated
  3. washwashed twice with 800 ml of water
  4. customAfter evaporating under reduced vacuum
  5. dissolutionthe residue is dissolved with 2.75 liters of methylene chloride
  6. temperatureat reflux
  7. customto return to ambient temperature
  8. stirringwith stirring
  9. temperatureis then cooled to 5° C
  10. filtrationThe crystals are filtered off
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-84907fc26de94815b70d44f254242640
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638657B2

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