Hydrochloric Acid → Methyl 4-hydroxy-2-isopropoxybenzoate

HRID 1008652Notes

Reaction equation

HRID 1008652 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-f83331669fe046e5b8c4a2c3297bd5c1
Source dataset
uspto-grants-2004_09
Patent number
US06797708B2

Reaction notes

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