2-Chlorobenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester → 3-(2-Chlorophenylsulfonyloxy)-5-methylphenol

HRID 482087

Reaction equation

HRID 482087 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][C:21]=2[Cl:26])(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[OH:8][C:9]1[CH:10]=[C:11]([O:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

4

Reactant 1

HCID 190649762-Chlorobenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester

Product 1

HCID 112779473-(2-Chlorophenylsulfonyloxy)-5-methylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chlorobenzenesulfonic acid 3-benzyloxy-5-methylphenyl ester (4.66 g, 12 mmol), as prepared in the preceding step, and 10% palladium on carbon (500 mg) in tetrahydrofuran (80 mL) was hydrogenated (balloon) for 3 h. The catalyst was removed by filtration through diatomaceous earth (tetrahydrofuran washes) and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (methylene chloride) to give the title compound as a pale-yellow solid (3.20 g, 89%, 1 H-NMR (300 MHz, CDCl3) δ 2.22 (s, 3H), 5.24 (s, 1H), 6.44 (t, 1H), 6.53 (d, 2H), 7.38 (dt, 1H), 7.60 (m, 2H), 7.96 (dd, 1H).

Workup

  1. customfor 3 h
  2. customThe catalyst was removed by filtration through diatomaceous earth (tetrahydrofuran washes)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-c8cec32e717c49cda57606d7deda4967
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Linked notes

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