Dimethyl Sulfide → 2-Hydroxyphenyl methanesulfonate

HRID 2239576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239576
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12]CC1C=CC=CC=1)(=[O:4])=[O:3].B(F)(F)F.CCOCC.CSC>C(Cl)Cl>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 866258732-(Benzyloxy)phenyl methanesulfonate

Produkt 1

HCID 132483392-Hydroxyphenyl methanesulfonateAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(Benzyloxy)phenyl methanesulfonate (4.00 g, 14.37 mmol) was dissolved in dry DCM (50 mL) under nitrogen atmosphere. Boron trifluoride diethyl etherate (8.16 g, 57.49 mmol) was added followed by dimethyl sulfide (3.57 g, 57.49 mmol) and the reaction mixture was stirred at rt overnight. The reaction mixture was poured onto ice and the aqueous layer was extracted with DCM. The organic layers were combined, washed with water, dried (Na2SO4), filtered and evaporated to give the title compound (2.49 g, 92%). 1H NMR (500 MHz, CDCl3): δ 3.26 (s, 3H), 6.16 (s, 1H), 6.96 (dt, 1H), 7.09 (dd, 1M), 7.22-7.28 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 37.74, 119.01, 121.65, 123.71, 129.09, 136.99, 148.43; Mass Spectrum: M−H+ 187.

Aufarbeitung

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe aqueous layer was extracted with DCM
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2ecf98af6e764a3ea094832299cdff4f
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723333B2

Notizen zur Reaktion

Wird geladen…