Hydrochloric Acid → Methyl 4-hydroxy-2-methoxybenzoate

HRID 1821523Notes

Reaction equation

HRID 1821523 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-3ccee06f95b84302b90440d956d3c7d5
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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