Potassium Hydroxide → HCID 19036696, compound

HRID 264353Notes

Reaction equation

HRID 264353 reaction equation
[CH2:1]([CH:3]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[C:8]([OH:16])[CH:7]=1)[CH3:2].[OH-].[K+]>CO>[CH2:1]([CH:3]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[C:8]([OH:16])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19036688HCID 19036688, compound2×

Product 1

HCID 19036696HCID 19036696, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 100 ml of methanol was dissolved 6.44 g (23.1 mmol) of methyl 4-(2-ethylhexyloxy)-2-hydroxybenzoate (compound 1 obtained in Example 1), and an aqueous solution of 3.0 g (53.5 mmol) of KOH was added thereto at room temperature to obtain a reaction mixture. The resulting reaction mixture was heated under reflux for 4 hours, followed by cooling to room temperature, and methanol was evaporated. The residue was poured into 200 ml of dilute hydrochloric acid to be rendered acidic and then extracted with 200 ml of ethyl acetate. The extract was washed successively with two 200 ml portions of water and two 200 ml portions of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated. Recrystallization of the resulting crude product from ethyl acetate/hexane gave 4.64 g (76%) of 4-(2-ethylhexyloxy)-2-hydroxybenzoic acid represented by the following chemical formula (hereinafter referred to as compound 14) as white crystals. The analytical results of the product are shown below. ##STR35##

Workup

  1. customat room temperature to obtain a reaction mixture
  2. customThe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux for 4 hours
  5. custommethanol was evaporated
  6. additionThe residue was poured into 200 ml of dilute hydrochloric acid
  7. extractionextracted with 200 ml of ethyl acetate
  8. washThe extract was washed successively with two 200 ml portions of water and two 200 ml portions of a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customRecrystallization of the resulting crude product from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0867e729d2224c1a9fa3cb9004a8f84f
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Reaction notes

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