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

HRID 10479Notes

Reaction equation

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

Participants

Conditions

Temperature: 30 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-001c79b908c44af0b3cbb88ecfd5d8af
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094809B2

Reaction notes

Loading…