Dimethyl Sulfide → 2-Hydroxyphenyl methanesulfonate

HRID 2239576Notes

Reaction equation

HRID 2239576 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 132483392-Hydroxyphenyl methanesulfonateYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2ecf98af6e764a3ea094832299cdff4f
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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