1-Naphthalenesulfonic acid 3-benzyloxy-5-methylphenyl ester → 5-Methyl-3-(1-naphthalenylsulfonyloxy)phenol

HRID 482108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482108
C([O:8][C:9]1[CH:10]=[C:11]([O:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([O:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1

Komponenten

4

Edukt 1

HCID 543310031-Naphthalenesulfonic acid 3-benzyloxy-5-methylphenyl ester

Produkt 1

HCID 539777205-Methyl-3-(1-naphthalenylsulfonyloxy)phenolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-naphthalenesulfonic acid 3-benzyloxy-5-methylphenyl ester (1.0 g, 2.47 mmol), as prepared in the preceding step, and 10% palladium on carbon (200 mg) in ethanol (20 mL) was hydrogenated (balloon) overnight. The catalyst was removed by filtration through diatomaceous earth (methanol washes) and the filtrate was evaporated in vacuo to give the title compound as a colorless syrup (705 mg, 91%). 1H-NMR (300 MHz, CDCl3) δ 2.11 (s, 3H), 4.20 (bs, 1H), 6.16 (t, 1H), 6.47 (t, 1H), 7.51 (t, 1H), 7.69 (t, 1H), 7.79 (t, 1H), 7.81 (d, 1H), 8.11 (dt, 2H), 8.77 (dd, 1H).

Aufarbeitung

  1. custom(balloon) overnight
  2. customThe catalyst was removed by filtration through diatomaceous earth (methanol washes)
  3. customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1bbf5b02dc07419398b27c7f0d1c0099
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792769

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