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

HRID 482087

Reaktionsgleichung

Reaktionsgleichung von HRID 482087
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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c8cec32e717c49cda57606d7deda4967
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792769

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