1-Naphthalenesulfonyl chloride → 5-Methyl-3-(1-naphthalenylsulfonyloxy)phenol

HRID 442955ノート

反応式

HRID 442955 の反応式
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[C:11]1([S:21](Cl)(=[O:23])=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>C([O-])(O)=O.[Na+].C(OCC)C.O>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:21]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)(=[O:23])=[O:22])[CH:3]=[C:4]([OH:5])[CH:6]=1

参加物

6

反応物 2

HCID 665601-Naphthalenesulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

生成物 1

HCID 539777205-Methyl-3-(1-naphthalenylsulfonyloxy)phenol収率 68.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Orcinol monohydrate (1.42 g, 10.0 mmol) and 1-naphthalenesulfonyl chloride (2.27 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 3% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (2.15 g, 68%). 1H-NMR (300 MHz, CDCl3) δ 8.79 (d, J=8.5 Hz, 1H), 8.14 (d, J=7.0 Hz, 2H), 7.98 (d, J=8.4 Hz, 1H), 7.78 (t, J=8.5 Hz, 1H), 7.67 (t, J=8.1 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 6.46 (s, 1H), 6.34 (s, 1H), 6.17 (s, 1H), 2.14 (s, 3H).

後処理

  1. extractionextracted into ethyl acetate (3×50 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was purified by flash column chromatography (dichloromethane to 3% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-3e6630cdbb1b46928c7693c90f9a5e37
出典データセット
uspto-grants-1999_04
特許番号
US05891909

反応ノート

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