Hydrochloric Acid → Methyl 4-hydroxy-2-isopropoxybenzoate

HRID 603981Notes

Reaction equation

HRID 603981 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-c3aea262c61f4cbbb68bca8546feef3a
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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