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

HRID 442955노트

반응식

HRID 442955 반응식
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

참가 물질

6

반응물 2

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

생성물 1

HCID 539777205-Methyl-3-(1-naphthalenylsulfonyloxy)phenol수율 68.4%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3e6630cdbb1b46928c7693c90f9a5e37
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891909

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