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

HRID 1020515ノート

反応式

HRID 1020515 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 667658085-Hydroxy-4'-trifluoromethyltolan収率 9,057.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
30 °C

実験手順

Compound 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 showed 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).

後処理

  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)

出典と根拠

ORDレコード
ord-37b75bad989549de9870aa7579524564
出典データセット
uspto-grants-2014_05
特許番号
US08716355B2

反応ノート

読み込み中…