Hydrochloric Acid → Methyl 4-hydroxy-2-isopropoxybenzoate

HRID 1821528Notes

Reaction equation

HRID 1821528 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([O:12]C(=O)C)=[CH:8][C:7]=1[O:16][CH:17]([CH3:19])[CH3:18].Cl>C1COCC1.CO.O>[CH3:3][O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[O:16][CH:17]([CH3:18])[CH3:19]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 670554964-Acetoxy-2-isopropoxy-benzoic acid methyl ester

Product 1

HCID 18398692Methyl 4-hydroxy-2-isopropoxybenzoateYield 115%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.1N NaOH (10 mL, 1 mmol) was added to a solution of 4-Acetoxy-2-isopropoxy-benzoic acid methyl ester (0.910 g, 3.6 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 0.870 g of 4-Hydroxy-2-isopropoxy-benzoic acid methyl ester in quantitative 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-2bd88845e23744d3b86b641729567f1c
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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