Sodium Methoxide → Methyl 2-hydroxy-3-(propan-2-yloxy)benzoate

HRID 577562Notes

Reaction equation

HRID 577562 reaction equation
C[C:2]1(C)[O:7][C:6]2[C:8]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:9][CH:10]=[CH:11][C:5]=2[C:4](=[O:16])[O:3]1.C[O-].[Na+]>CO>[OH:7][C:6]1[C:8]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:9][CH:10]=[CH:11][C:5]=1[C:4]([O:3][CH3:2])=[O:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 867237872,2-dimethyl-8-(propan-2-yloxy)-4H-1,3-benzodioxin-4-one

Product 1

HCID 85741171Methyl 2-hydroxy-3-(propan-2-yloxy)benzoateYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2,2-dimethyl-8-(propan-2-yloxy)-4H-1,3-benzodioxin-4-one (123b, 1.40 g, 5.92 mmol) in methanol (12 mL) was treated with sodium methoxide in methanol (0.5 M, 24 mL, 12 mmol) and stirred at room temperature for 3 hours, 40 minutes. The solvents were evaporated and the residue partitioned between ammonium chloride solution (sat., aq., 20 mL) and ethyl acetate (2×30 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under vacuum to give methyl 2-hydroxy-3-(propan-2-yloxy)benzoate (123c, 1.24 g, 93% yield) as a colorless liquid.

Workup

  1. customThe solvents were evaporated
  2. customthe residue partitioned between ammonium chloride solution (sat., aq., 20 mL) and ethyl acetate (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-da9a4bd7e6344ae5b9e88a6220ef9a3d
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

Loading…