2-Chlorobenzenesulfonic acid 3-benzyloxyphenyl ester → 2-Chlorobenzenesulfonic acid 3-hydroxyphenyl ester

HRID 2227595Notes

Reaction equation

HRID 2227595 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([O:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>O1CCCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([O:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 542636472-Chlorobenzenesulfonic acid 3-benzyloxyphenyl ester

Product 1

HCID 540152812-Chlorobenzenesulfonic acid 3-hydroxyphenyl esterYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Chlorobenzenesulfonic acid 3-benzyloxyphenyl ester (3.75 g, 10 mmol), as prepared in the preceding step, Pd/C (10%) (350 mg) in tetrahydrofuran (80 mL) was hydrogenated (balloon) for 3 h. The catalyst was filtered through Celite and washed with tetrahydrofuiran. The combined tetrahydrofuran solution was evaporated in vacuo and the residue was then purified by flash column chromatography (methylene chloride) to give the title compound as a colorless oil (2.75 g, 95%). 1H-NMR (300 MHz, CDCl3) δ 6.68 (m, 3 H), 7.12 (t, 1H, J=6.5 Hz), 7.37 (t, 1 H, J=7.1 Hz), 7.60 (m, 2 H), 7.94 (dd, 1 H, J=0.6, 4.0 Hz).

Workup

  1. customfor 3 h
  2. filtrationThe catalyst was filtered through Celite
  3. washwashed with tetrahydrofuiran
  4. customThe combined tetrahydrofuran solution was evaporated in vacuo
  5. customthe residue was then purified by flash column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-44c478316b4641a999b494078d5df7bb
Source dataset
uspto-grants-2002_07
Patent number
US06414020B2

Reaction notes

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