3-Trifluoromethylbenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester → 3-Trifluoromethylbenzenesulfonic acid 3-hydroxy-5-methylphenyl ester

HRID 482110Notes

Reaction equation

HRID 482110 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([O:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([O:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

4

Reactant 1

HCID 542835923-Trifluoromethylbenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester

Product 1

HCID 540717503-Trifluoromethylbenzenesulfonic acid 3-hydroxy-5-methylphenyl esterYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-trifluoromethylbenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester (633 mg, 1.5 mmol), as prepared in the preceding step, and 10% palladium on carbon (100 mg) in ethanol (20 mL) was hydrogenated (balloon) for 3 h. The catalyst was removed by filtration through diatomaceous earth (methanol washes) and the filtrate was evaporated in vacuo to give the title compound as a colorless syrup (485 mg, 97%). 1H-NMR (300 MHz, CDCl3 /CD3OD) δ 2.20 (s, 3H), 6.26 (s, 1H), 6.30 (t, 1H), 6.57 (s, 1H), 7.74 (t, 1H), 7.96 (d, 1H), 8.05 (d, 1H), 8.09 (s, 1H).

Workup

  1. customfor 3 h
  2. customThe catalyst was removed by filtration through diatomaceous earth (methanol washes)
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-67fde44ca65b4cc59fd4e30bf4bb8e3e
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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