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

HRID 482087

반응식

HRID 482087 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c8cec32e717c49cda57606d7deda4967
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792769

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