Water → HCID 23147631, compound

HRID 505656Notes

Reaction equation

HRID 505656 reaction equation
[C:1]([CH2:4][C:5]1[C:13]([CH2:14][CH3:15])=[C:12]([O:16][CH2:17][O:18][CH3:19])[CH:11]=[C:10]([O:20][CH2:21][O:22][CH3:23])[C:6]=1[C:7]([OH:9])=[O:8])([OH:3])=[O:2].[C:24](OC(=O)C)(=O)C.O.C[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:14]([C:13]1[C:5]([CH2:4][C:1]([O:3][CH3:24])=[O:2])=[C:6]([C:10]([O:20][CH2:21][O:22][CH3:23])=[CH:11][C:12]=1[O:16][CH2:17][O:18][CH3:19])[C:7]([OH:9])=[O:8])[CH3:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 7918Acetic AnhydrideHCID 10942334Sodium MethoxideHCID 23147512HCID 23147512, compound

Product 1

HCID 23147631HCID 23147631, compoundYield 126.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The above-obtained 2-(carboxymethyl)-3-ethyl-4,6-bis(methoxymethoxy)benzoic acid (0.38 g, 1.2 mmol) was dissolved in toluene (20 mL) and the obtained solution was added with acetic anhydride (0.20 mL, 2.1 mmol), followed by stirring at 100° C. for 4 hours. The reaction mixture was added with water and then extracted with diethylether 3 times. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. Then, the solvent was evaporated under reduced pressure and the obtained residue was dissolved in methanol (20 mL). The obtained solution was added with sodium methoxide (0.22 g, 4.2 mmol) and stirred at a room temperature for 7 hours. After adding water, the reaction mixture was extracted with ethyl acetate 3 times. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. Then, the solvent was evaporated under reduced pressure to obtain 3-ethyl-2-(methoxycarbonylmethyl)-4,6-bis(methoxymethoxy)benzoic acid (0.52 g, 100%).

Workup

  1. extractionextracted with diethylether 3 times
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThen, the solvent was evaporated under reduced pressure
  5. dissolutionthe obtained residue was dissolved in methanol (20 mL)
  6. stirringstirred at a room temperature for 7 hours
  7. extractionthe reaction mixture was extracted with ethyl acetate 3 times
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fa6c513bef814edcbe3e3d3a82aa974b
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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