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

HRID 1020515Notes

Reaction equation

HRID 1020515 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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-37b75bad989549de9870aa7579524564
Source dataset
uspto-grants-2014_05
Patent number
US08716355B2

Reaction notes

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