Hydrochloric Acid → Benzyl 3-hydroxyphenyl ether

HRID 651534Notes

Reaction equation

HRID 651534 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)(=O)C.[OH-].[Na+].Cl>O1CCCC1>[CH2:12]([O:11][C:7]1[CH:6]=[C:5]([OH:4])[CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 223458653-Benzyloxyphenyl acetate

Product 1

HCID 138048Benzyl 3-hydroxyphenyl etherYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Benzyloxyphenyl acetate (4.84 g, 20 mmol), as prepared in the preceding step, in tetrahydrofuran (50 mL) was treated with 1 N NaOH (30 mL) at room temperature for 3 h. The mixture was acidified with 1 N HCl and extracted with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. The solvent was removed in vacuo and the residue purified by flash column chromatography (methylene chloride) to give the title compound as a colorless liquid (3.80 g, 96%).

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by flash column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-4630dc38332540efb92661ade97ed0bd
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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