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

HRID 322946Notes

Reaction equation

HRID 322946 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-].[Na+]>CO>[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 14798Sodium HydroxideHCID 106826256-Benzyloxy-1,3-benzoxathiol-2-one

Product 1

HCID 219047055-(Benzyloxy)-2-sulfanylphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-benzyloxy-1,3-benzoxathiol-2-one (35 g), aqueous sodium hydroxide solution (200 mL; 2 N) and methanol (50 mL) is stirred at ambient temperature for 16 hours and then it is heated at reflux for 30 minutes. The reaction mixture is then evaporated to dryness and the residue is acidified to pH 1 by treatment with concentrated hydrochloric acid (20 mL). The residue is diluted with water (200 mL) and then extracted with diethyl ether (3×200 mL). The combined organic extracts are washed with brine (100 mL), dried over magnesium sulphate, filtered and concentrated in vacuo, to give 5-benzyloxy-2-mercaptophenol, in the form of a yellow oil which solidified on standing overnight.

Workup

  1. temperatureit is heated
  2. temperatureat reflux for 30 minutes
  3. customThe reaction mixture is then evaporated to dryness
  4. additionThe residue is diluted with water (200 mL)
  5. extractionextracted with diethyl ether (3×200 mL)
  6. washThe combined organic extracts are washed with brine (100 mL)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88694364a4a04c1f8fba9618b2539281
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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