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

HRID 482108Notes

Reaction equation

HRID 482108 reaction equation
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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1bbf5b02dc07419398b27c7f0d1c0099
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

Loading…