2-Cyanobenzenesulfonyl Chloride → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol Hydrochloride

HRID 1059461

Reaktionsgleichung

Reaktionsgleichung von HRID 1059461
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)(=[O:11])=[O:10])#[N:2].O.[C:22]1(O)C=C(C)C=[C:24]([OH:25])[CH:23]=1.C(C1C=CC=CC=1S([Cl:42])(=O)=O)#N>C([O-])(O)=O.[Na+].C(OCC)C.O>[ClH:42].[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:20][CH2:22][CH2:23][CH2:24][OH:25])(=[O:11])=[O:10])#[N:2]

Komponenten

7

Edukt 3

HCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 227226433-(2-Cyanophenylsulfonyloxy)-5-methylphenol

Produkt 1

HCID 186697053-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol HydrochlorideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

3-(2-Cyanophenylsulfonyloxy)-5-methylphenol: Orcinol monohydrate (1.42 g, 10.0 mmol) and 2-cyanobenzenesulfonyl chloride (2.02 g, 10.0 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room 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 5% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.65 g, 57%). 1H-NMR (300 MHz, CDCl3) δ 8.07 (m, 1H), 7.94 (m, 1H), 7.75-7.80 (m, 2H), 6.57 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 5.69 (br s, 1H), 2.22 (s, 3H).

Aufarbeitung

  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 5% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-b6531c9ea60c4c6a95928a78653eabc6
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518310B2

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