Potassium Hydroxide → 4-Methoxy-2-(prop-2-en-1-yloxy)benzoic acid

HRID 1864735Notes

Reaction equation

HRID 1864735 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8])[CH:2]=[CH2:3].[OH-].[K+]>CO.CCOC(C)=O>[CH2:1]([O:4][C:5]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 10242646Methyl 2-(allyloxy)-4-methoxybenzoate

Product 1

HCID 215068784-Methoxy-2-(prop-2-en-1-yloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2 (20.5 g, 11 mmol) in aqueous methanol (30 mL) was added KOH (1 eq, 630 mg). Reaction was heated to 50° C. for 12 hours before the addition of more KOH (630 mg). After 12 hours, the mixture was cooled, diluted with EtOAc and washed with 1M HCl. Aqueous layer was extracted with EtOAc (3×). Combined organic layers, dried over Na2SO4, and concentrated. Product was isolated as an off white solid and used without further purification.

Workup

  1. customReaction
  2. temperaturethe mixture was cooled
  3. washwashed with 1M HCl
  4. extractionAqueous layer was extracted with EtOAc (3×)
  5. dry with materialCombined organic layers, dried over Na2SO4
  6. concentrationconcentrated
  7. customProduct was isolated as an off white solid
  8. customused without further purification

Sources & evidence

ORD record
ord-565f855c9e2e4c9ba645ebd6f42aab41
Source dataset
uspto-grants-2009_12
Patent number
US07625933B2

Reaction notes

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