Dichloromethane → 5-Methyl-3-(3-pyridinylsulfonyloxy)phenol

HRID 442970

Reaktionsgleichung

Reaktionsgleichung von HRID 442970
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:13]=1.ClCCl>C(=O)(O)[O-].[Na+]>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:18]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)(=[O:20])=[O:19])[CH:3]=[C:4]([OH:5])[CH:6]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 12571517Pyridine-3-sulfonyl chloride hydrochloride

Produkt 1

HCID 544756955-Methyl-3-(3-pyridinylsulfonyloxy)phenolAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of orcinol monohydrate (1.42 g, 0.01 mol) and 3-pyridylsulfonyl chloride hydrochloride (2.13 g, 0.01 mol), as prepared in J. Am. Chem. Soc., 114:4889 (1992), in saturated aqueous sodium bicarbonate (17.5 mL) and dichloromethane (50 mL) was stirred rapidly at ambient temperature for 2 days. The dichloromethane was separated and the aqueous layer was extracted with ethyl acetate (3×25 mL). The ethyl acetate and dichloromethane extracts were combined and washed with brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was recrystallized from ether and hexane, collected by filtration, and dried under high vacuum to give 1.54 g of a white solid (58% yield). 1H-NMR (300 MHz, CDCl3) δ 9.03 (d, 1H), 8.88 (dd, 1H), 8.16 (dt, 1H), 7.5 (m, 1H), 6.57 (d, 1H), 6.42 (s, 1H), 6.32 (t, 1H), 2.24 (s, 3H).

Aufarbeitung

  1. customas prepared in J
  2. customThe dichloromethane was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×25 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was recrystallized from ether and hexane
  8. filtrationcollected by filtration
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a7647b352ca74818b082d564aa5e5e97
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891909

Verknüpfte Notizen

Wird geladen…