Hydrochloric Acid → Ethanol, 2-[4-(methylsulfonyl)phenoxy]-

HRID 1272047Notes

Reaction equation

HRID 1272047 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+].[O:14]1C=CC=[CH:16][CH:15]1OCCBr.Cl>CO.CC(N(C)C)=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][CH2:15][OH:14])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1233504-(Methylsulfonyl)phenolHCID 184563812-(2-Bromoethoxy)-2H-pyran

Product 1

HCID 14855255Ethanol, 2-[4-(methylsulfonyl)phenoxy]-Yield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-methanesulfonylphenol (1.72 g, 10 mmol), DMA (25 ml) and 4 N sodium hydroxide (7 ml) was stirred under an atmosphere of nitrogen. 2-(2-Pyranyloxy)ethylbromide (2.8 g, 14 mmol) was added dropwise and then the mixture was stirred overnight at ambient temperature. The solvent was evaporated in vacuo and the residue was taken up in water (100 ml). The aqueous mixture was extracted with ethyl acetate (2×100 ml) and the combined organic extracts were washed with a 0.5 N sodium hydroxide solution and brine. The organic phase was concentrated to give an oily residue that was dissolved in methanol (50 ml). A solution of 5 N HCl (20 ml) was added and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated and a small portion of ice was added followed by 4 N sodium hydroxide until approximately pH 10. The alkaline mixture was extracted with ethyl acetate (3×75 ml) and the combined organic extracts were washed with water and dried (MgSO4). The solvent was evaporated to give 0.82 g (38%) of 2-(4-methanesulfonylphenoxy)ethanol. M.p. 89–90° C.

Workup

  1. stirringthe mixture was stirred overnight at ambient temperature
  2. customThe solvent was evaporated in vacuo
  3. extractionThe aqueous mixture was extracted with ethyl acetate (2×100 ml)
  4. washthe combined organic extracts were washed with a 0.5 N sodium hydroxide solution and brine
  5. concentrationThe organic phase was concentrated
  6. customto give an oily residue that
  7. stirringthe mixture was stirred at ambient temperature for 2 hours
  8. concentrationThe reaction mixture was concentrated
  9. additiona small portion of ice was added
  10. extractionThe alkaline mixture was extracted with ethyl acetate (3×75 ml)
  11. washthe combined organic extracts were washed with water
  12. dry with materialdried (MgSO4)
  13. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6a2ef0e3a4dd489f9cba813ac9a1308d
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

Loading…