Hydrochloric Acid → Benzyl 3-hydroxyphenyl ether

HRID 1976103Notes

Reaction equation

HRID 1976103 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%). 1H-NMR (300 MHz, CDCl3) δ 5.01 (s, 2 H), 5.09 (s, 1 H), 6.47 (t, 2 H, J=2.2 Hz), 6.56 (dd, 1 H, J=1.1, 4.1 Hz), 7.11 (t, 1 H), and 7.39 (m, 5 H).

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-5d1564cf30524c969989729b417ebb2f
Source dataset
uspto-grants-2001_05
Patent number
US06225302B1

Reaction notes

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