Dimethyl Sulfide → 4-Hydroxyphenyl methanesulfonate

HRID 2239587Notes

Reaction equation

HRID 2239587 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][CH:7]=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][C:9]([OH:12])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 86625878HCID 86625878, compound

Product 1

HCID 5729984-Hydroxyphenyl methanesulfonateYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Benzyloxy)phenyl methanesulfonate (5.31 g, 19.08 mmol) was dissolved in dry DCM (70 mL) under nitrogen atmosphere. Boron trifluoride diethyl etherate (10.83 g, 76.31 mmol) was added followed by dimethyl sulfide (4.74 g, 76.31 mmol) and the reaction mixture was stirred at rt for 3 h. The reaction mixture was poured onto ice and the aqueous layer was extracted with DCM. The organic layers were combined, washed with water, dried over Na2SO4, filtered and evaporated to give the title compound (2.96 g, 82.5%). 1H NMR (500 MHz, CDCl3): δ 3.14 (s, 3H), 5.51 (s, 1H), 6.83 (d, 2H), 7.14 (d, 2H); 13C NMR (125 MHz, CDCl3): δ 37.35, 116.74, 123.49, 142.68, 155.06.

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 over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4d76bbafa12146668d66a7c915a43c60
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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