Hydrochloric Acid → 3-Methoxy-4-(methoxycarbonyl)benzoic acid

HRID 1377677Notes

Reaction equation

HRID 1377677 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]([O:15][CH3:16])=[O:14].O.[OH-].[Na+].Cl>C1COCC1>[CH3:16][O:15][C:13]([C:4]1[CH:5]=[CH:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:3]=1[O:2][CH3:1])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18677354Dimethyl 2-methoxybenzene-1,4-dicarboxylate

Product 1

HCID 123983053-Methoxy-4-(methoxycarbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxy-1,4-bis (methoxycarbonyl)benzene (1.61 g, 7.20 mmol) from Step 2 was dissolved in 20 mL of 1:1 THF:H2O and to the stirred solution was added 1N NaOH (7.2 mL, 7.2 mmol). After 24 h, the reaction was acidified to pH 2 with 1N HCl. The reaction was concentrated under reduced pressure and then extracted with CHCl3. The CHCl3 layer was dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 93:7 CHCl3 :A, where A=95:5 MeOH:HOAc. 1-Methoxycarbonyl-2-methoxybenzene 4-carboxylic acid was obtained as an oil (30% yield).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. extractionextracted with CHCl3
  3. dry with materialThe CHCl3 layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-b4f68404c43d49ef8cc2bd6d2db573e2
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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