Hydrochloric Acid → 4-ALLYLSULFANYL-PHENOL

HRID 418558Notes

Reaction equation

HRID 418558 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[CH:16]=[CH2:17].Cl>CN(C=O)C>[CH2:17]([S:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Product 1

HCID 53241974-ALLYLSULFANYL-PHENOLYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-hydroxythiophenol (1.6) (4.30 g, 34.1 mmol) in DMF (25 mL) were added K2CO3 (4.71 g, 34.1 mmol) and allyl bromide (3.09 mL, 34.1 mmol) at ice-water temperature, and the mixture was stirred for 15 minutes, prior to stirring overnight at room temperature. After the addition of 1 M aqueous HCl, the mixture was extracted with ether (3×). The combined organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10 to 1/6) to give 1.7 (5.74 g, 70%) as a white semi-solid. The 1H and 13C NMR spectra and mass spectrum were identical to the reported values (Tetrahedron 1994, 50, 10321-10330).

Workup

  1. stirringto stirring overnight at room temperature
  2. extractionthe mixture was extracted with ether (3×)
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10 to 1/6)

Sources & evidence

ORD record
ord-e37230d5c3574e98834df6b3cf175552
Source dataset
uspto-grants-2012_01
Patent number
US08093287B2

Reaction notes

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