Hydrochloric Acid → Methyl 2-hydroxy-4-isopropoxybenzoate

HRID 2293537Notes

Reaction equation

HRID 2293537 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:19](I)([CH3:21])[CH3:20].Cl>CC(C)=O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:19]([CH3:21])[CH3:20])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 23244891Methyl 2-hydroxy-4-isopropoxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 1.50 g portion of methyl 2,4-dihydroxybenzoate was dissolved in 30 ml of acetone, and 3.10 g of potassium carbonate and 1.7 ml of isopropyl iodide were added, followed by 48 hours of heating under reflux. After completion of the reaction, the reaction solution was poured into 1N hydrochloric acid aqueous solution, extracted with chloroform and dried over anhydrous sodium sulfate and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1) to give 1.60 g of methyl 2-hydroxy-4-isopropoxybenzoate.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1)

Sources & evidence

ORD record
ord-33be7e034ca845a8b610442816256930
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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