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

HRID 368544

Reaktionsgleichung

Reaktionsgleichung von HRID 368544
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

Komponenten

4

Edukt 1

HCID 542636472-Chlorobenzenesulfonic acid 3-benzyloxyphenyl ester

Produkt 1

HCID 540152812-Chlorobenzenesulfonic acid 3-hydroxyphenyl esterAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-fdea59b8637546e0b6774de4ed7839b7
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133315

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