Methanol → 3-(Allyloxy)phenol

HRID 1370830Notes

Reaction equation

HRID 1370830 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]=[CH2:14])[CH:6]=1)(=O)C.[OH-].[Na+].CO>C1COCC1>[CH2:12]([O:11][C:7]1[CH:6]=[C:5]([OH:4])[CH:10]=[CH:9][CH:8]=1)[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 112755383-(allyloxy)phenyl Acetate

Product 1

HCID 53141523-(Allyloxy)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 61A (7.19 g, 37.4 mmoles) in THF (30 mL) was treated with 4N NaOH (19 mL, 75 mmoles) and MeOH (5 mL). After one hour, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with aqueous NH4Cl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide the title compound without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous NH4Cl, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-83b92bd422474d3b90f45bf086b1dfbf
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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