Sodium Hydroxide → 4-((3,5,6-Trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acid

HRID 1803025Notes

Reaction equation

HRID 1803025 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:28])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH2:16][C:17]2[C:22]([CH3:23])=[N:21][C:20]([CH3:24])=[C:19]([CH3:25])[N:18]=2)=[C:9]([O:26][CH3:27])[CH:8]=1)C>O>[CH3:23][C:22]1[C:17]([CH2:16][O:15][C:10]2[C:9]([O:26][CH3:27])=[CH:8][C:7]([C:6]([OH:28])=[O:5])=[CH:12][C:11]=2[O:13][CH3:14])=[N:18][C:19]([CH3:25])=[C:20]([CH3:24])[N:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 594799224-((3,5,6-Trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acid ethyl ester

Product 1

HCID 594799214-((3,5,6-Trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Adding water (20 mL), NaOH (0.14 g, 3.5 mmol) into a 100 mL round-bottom flask, stirring to dissolve, then adding 95% alcohol (20 mL), 4-((3,5,6-trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acid ethyl ester (1.00 g, 2.8 mmol), stifling under room temperature to react for 4 hours, TLC [V(petroleum ether):V(ethyl acetate)=3:1 as developing agent] detecting shows that reaction is complete, (Rf of raw material=0.5, Rf of product=0), distilling out the alcohol under reduced pressure, adjusting pH of the reaction solution to 4-5 with 1.0M HCl while keeping the reaction solution cool to separate out solid, filtering, washing the solid with cool water for three times, processing with vacuum filtration, recrystallizing with anhydrous alcohol, drying under 70° C. for 8 hours to obtain 0.88 g white crystalloid of 4-((3,5,6-trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acid, wherein a yield is 95.4%, m.p.>218° C. (dec).

Workup

  1. dissolutionto dissolve
  2. customstifling under room temperature
  3. customto react for 4 hours
  4. distillation(Rf of raw material=0.5, Rf of product=0), distilling out the alcohol under reduced pressure
  5. temperaturecool
  6. customto separate out solid
  7. filtrationfiltering
  8. washwashing the solid with cool water for three times
  9. filtrationprocessing with vacuum filtration
  10. customrecrystallizing with anhydrous alcohol
  11. customdrying under 70° C. for 8 hours

Sources & evidence

ORD record
ord-9900bc4073c44ae2a5bfc221b62585aa
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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