Potassium Hydroxide → 5-(Benzyloxy)-2-sulfanylphenol

HRID 732756Notes

Reaction equation

HRID 732756 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]2[S:13]C(=O)[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([SH:13])=[C:11]([OH:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 106826256-Benzyloxy-1,3-benzoxathiol-2-one

Product 1

HCID 219047055-(Benzyloxy)-2-sulfanylphenolYield 81.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve 6-benzyloxy-benzo[1,3]oxathiol-2-one (24.33 g, 94.29 mmol) in dioxane (1000 mL) and add a KOH solution (94.29 mL, 188 mmol, 2M in water) with stirring. Flush the flask with N2 and then heat the reaction mixture to 80° C. for 2 hours. Cool the reaction mixture to room temperature and remove the solvent under reduced pressure. Adjust the pH to <2 with HCl (200 mL, 1.0 M in water). Extract the aqueous layer with EtOAc (3×500 mL). Combine the organic layers and dry with Na2SO4, filter and concentrate to give 17.8 g of 5-benzyloxy-2-mercapto-phenol (81.4%).

Workup

  1. customFlush the flask with N2
  2. temperatureCool the reaction mixture to room temperature
  3. customremove the solvent under reduced pressure
  4. extractionExtract the aqueous layer with EtOAc (3×500 mL)
  5. dry with materialCombine the organic layers and dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-5750c7f2ce7b4585821dc1ee1b60bb66
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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