Hydrochloric Acid → HCID 23147512, compound

HRID 505655Notes

Reaction equation

HRID 505655 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[CH:8][C:7]([O:14][CH2:15][O:16][CH3:17])=[C:6]([CH2:18][CH3:19])[C:5]=1[CH2:20][C:21]([O:23]C)=[O:22].[OH-].[Li+].O.Cl>CO>[C:21]([CH2:20][C:5]1[C:6]([CH2:18][CH3:19])=[C:7]([O:14][CH2:15][O:16][CH3:17])[CH:8]=[C:9]([O:10][CH2:11][O:12][CH3:13])[C:4]=1[C:3]([OH:25])=[O:2])([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 23146994HCID 23146994, compound

Product 1

HCID 23147512HCID 23147512, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The above-obtained 3-ethyl-2-(methoxycarbonylmethyl)-4,6-bis(methoxymethoxy)benzoic acid methyl ester (1.1 g, 3.0 mmol) was dissolved in methanol (3 mL) and the obtained solution was added with 4.0 mol/L aqueous lithium hydroxide solution (15 mL, 60 mmol) followed by stirring at 60° C. for 30 hours. The reaction mixture was added with water and 6.0 mol/L hydrochloric acid and the pH value was adjusted to 3. Then, the mixture was extracted with ethyl acetate 3 times. The organic layers were combined and dried over anhydrous sodium sulfate. Then, the solvent was evaporated under reduced pressure to obtain 2-(carboxymethyl)-3-ethyl-4,6-bis(methoxymethoxy)benzoic acid (0.91 g, 94%).

Workup

  1. extractionThen, the mixture was extracted with ethyl acetate 3 times
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a0e514f46b484d07aa49bc8df0bb9ac8
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

Loading…