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

HRID 482087ノート

反応式

HRID 482087 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c8cec32e717c49cda57606d7deda4967
出典データセット
uspto-grants-1998_08
特許番号
US05792769

反応ノート

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