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

HRID 368544

Reaction equation

HRID 368544 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 tetrahydrofuran. 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, 1H, J=7.1 Hz), 7.60 (m, 2 H), 7.94 (dd, 1H, J=0.6, 4.0 Hz).

Workup

  1. customfor 3 h
  2. filtrationThe catalyst was filtered through Celite
  3. washwashed with tetrahydrofuran
  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-fdea59b8637546e0b6774de4ed7839b7
Source dataset
uspto-grants-2000_10
Patent number
US06133315

Linked notes

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