Hydrochloric Acid → Methyl 4-hydroxy-2-methoxybenzoate

HRID 603976Notes

Reaction equation

HRID 603976 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([O:12]C(=O)C)=[CH:8][C:7]=1[O:16][CH3:17].Cl>C1COCC1.CO.O>[CH3:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[O:16][CH3:17]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 534162044-Acetoxy-2-methoxy-benzoic acid methyl ester

Product 1

HCID 12532676Methyl 4-hydroxy-2-methoxybenzoateYield 33%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.1N NaOH (10 mL, 1 mmol) was added to a solution of the product of step 2 (1.10 g, 4.9 mmol) in THF (1 mL) and MeOH (1 mL). Reaction was stirred for three days at room temperature. Reaction solution was concentrated by rotary evaporation and resulting residue was dissolved in water. The solution was neutralized with 1N HCl and a precipitate formed. Collected precipitate and washed with water and hexane. Obtained 0.29 g of 4-Hydroxy-2-methoxy-benzoic acid methyl ester in 33% yield.

Workup

  1. customReaction
  2. customReaction solution
  3. concentrationwas concentrated by rotary evaporation
  4. customresulting residue
  5. customa precipitate formed
  6. customCollected precipitate
  7. washwashed with water and hexane

Sources & evidence

ORD record
ord-d93a75c9507044b2ba3efd0c3c07995a
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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