p-Toluenesulfonic acid → 5-Hydroxy-4'-trifluoromethyltolan

HRID 10479노트

반응식

HRID 10479 반응식
O1CCCCC1O[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:10][CH:9]=1.C(Cl)Cl.CC1C=CC(S(O)(=O)=[O:37])=CC=1>CO>[OH:37][C:9]1[CH:8]=[CH:13][CH:12]=[C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[CH:10]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 582885584-Tetrahydropyranyloxy-4'-trifluormethyltolan

생성물 1

HCID 667658085-Hydroxy-4'-trifluoromethyltolan수율 9,057.1%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
30 °C

실험 절차

Coumpound 4 (13.84 g, 40 mmol), CH2Cl2 (75 ml) and MeOH (125 ml) were placed in a 250 ml round bottomed flask, then TsOH (0.4 g, 0.4 mmol) was added. The reaction mixture was stirred at 30° C. for 1 hour. When the reaction was finished (TLC shows no starting material remaining), the solvent was removed by rotary evaporation and the residue was dissolved in EtOAc and filtered through silica gel. The solvent was removed and the solid was recrystallized from solvents of ethyl acetate and hexane (1:5) to give a pale yellow crystal 9.5 g (90%), mp 131–132° C., δH(CDCl3; 300 MHz): 7.59(s, 4H, Ar—H), 7.44(d, J=8.7, 2H, Ar—H), 6.82(d, J−8.7, 2H, Ar—H), 5.16(s, 1H, OH).

후처리

  1. customwas removed by rotary evaporation
  2. dissolutionthe residue was dissolved in EtOAc
  3. filtrationfiltered through silica gel
  4. customThe solvent was removed
  5. customthe solid was recrystallized from solvents of ethyl acetate and hexane (1:5)

출처 및 근거

ORD 기록
ord-001c79b908c44af0b3cbb88ecfd5d8af
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094809B2

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