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

HRID 482113

Reaction equation

HRID 482113 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]=[CH:22][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:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

4

Reactant 1

HCID 54005214Benzenesulfonic acid 3-benzyloxy-5-methylphenyl ester

Product 1

HCID 11054545Benzenesulfonic acid 3-hydroxy-5-methylphenyl esterYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzenesulfonic acid 3-benzyloxy-5-methylphenyl ester (532 mg, 1.5 mmol), as prepared in the preceding step, and 10% palladium on carbon (200 mg) in ethanol (20 mL) was hydrogenated (balloon) overnight. The catalyst was removed by filtering over diatomaceous earth and the filtrate was evaporated in vacuo to give the title compound as a colorless syrup (390 mg, 98%). 1H-NMR (300 MHz, CDCl3 /CD3OD) δ 2.19 (s, 3H), 6.27 (s, 1H), 6.54 (s, 1H), 6.66 (s 1H), 7.43 (m, 1H), 7.55 (t, 1H), 7.70 (t, 1H), 7.85 (m, 2H).

Workup

  1. custom(balloon) overnight
  2. customThe catalyst was removed
  3. filtrationby filtering over diatomaceous earth
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-07fbf5c563664a749808f9942eb4a60d
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Linked notes

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