Methanol → HCID 71278795, compound

HRID 1749720Notes

Reaction equation

HRID 1749720 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:19])[C:6]([O:13][CH2:14][C:15]([O:17]C)=[O:16])=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9].CO.[OH-].[Na+]>O>[C:15]([CH2:14][O:13][C:6]1[C:5]([CH3:19])=[CH:4][C:3]([O:2][CH3:1])=[CH:12][C:7]=1[C:8]([OH:10])=[O:9])([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 71278892HCID 71278892, compound

Product 1

HCID 71278795HCID 71278795, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

The synthesis was performed with reference to the known literature (Bioorganic & Medicinal Chemistry Letters, Vol. 17, p. 6354, 2007). Methyl 5-methoxy-2-(2-methoxy-2-oxoethoxy)-3-methylbenzoate (4.9 g, 18.3 mmol) was added with methanol (30 mL), and water (10 mL), and then added with sodium hydroxide (2.2 g, 55 mmol), and the mixture was stirred at 55° C. for 2 hours. The solvent was evaporated under reduced pressure, the residue was made acidic with 3 N hydrochloric acid, and then extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the solid formed was dried to obtain 2-(carboxymethoxy)-5-methoxy-3-methylbenzoic acid (3.9 g, 89%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe solid formed
  7. customwas dried

Sources & evidence

ORD record
ord-ed2065a50e244ed8b2590dfdec84ff01
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…