Tetrahydrofuran → 5-(Allyloxy)-2-sulfanylphenol

HRID 724268Notes

Reaction equation

HRID 724268 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]2[S:9]C(=O)[O:11][C:7]=2[CH:6]=1)[CH:2]=[CH2:3].C1COCC1>[OH-].[Na+]>[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([SH:9])=[C:7]([OH:11])[CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 14085935HCID 14085935, compound

Product 1

HCID 218771835-(Allyloxy)-2-sulfanylphenol

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

6-(Allyloxy)-1,3-benzoxathiol-2-one (48.3 g, 0.232 mol) was dissolved in aq. NaOH solution (2M, 300 ml) and THF (300 ml) to give a yellow solution which stirred at RT for 2 h. The THF was removed in vacuo, a small amount of precipitated starting material removed by filtration, and further starting material was removed by extraction of the aqueous phase into diethyl ether (3×300 ml). The aqueous phase was then acidified to pH 1 with cHCl (˜150 ml) with ice-cooling. Gas evolution was observed, and after 15 min, the title compound was obtained following extraction into diethyl ether (3×300 ml), drying over MgSO4 and concentration to a yellow oil (37.84 g, 0.18 mol).

Workup

  1. customThe THF was removed in vacuo
  2. customa small amount of precipitated
  3. customremoved by filtration
  4. customwas removed by extraction of the aqueous phase into diethyl ether (3×300 ml)
  5. temperaturecooling
  6. waitafter 15 min

Sources & evidence

ORD record
ord-ea810cd9ded043fabde4695d423c7123
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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