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

HRID 1191969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191969
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 667658085-Hydroxy-4'-trifluoromethyltolanAusbeute 9.057,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-547d514425924e29ace0eeeda1b21e7b
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680142B2

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