Water → 3-(3,4-dimethoxyphenyl)prop-2-ynoic Acid

HRID 1488943Notes

Reaction equation

HRID 1488943 reaction equation
[OH-].[K+].O.C([O:6][C:7](=[O:22])[CH:8](Br)[CH:9](Br)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)C>C(O)C>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:9]#[C:8][C:7]([OH:22])=[O:6])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11188645HCID 11188645, compound

Product 1

HCID 37083353-(3,4-dimethoxyphenyl)prop-2-ynoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 52.7 g (0.80 mol) of potassium hydroxide (85%) in 300 ml of ethanol and 30 ml of water 59.4 g (0.15 mol) of 2,3-dibromo-3-(3,4-dimethoxyphenyl)propionic acid ethyl ester are added at 25° C. over 10 minutes. The mixture is stirred under reflux for 2.5 hours. The solvent is evaporated, the residue dissolved in 200 ml of water and, with cooling to 10° C., the solution acidified with 2N hydrochloric acid. The resulting crystals are filtered off, washed with water and recrystallized from methanol/water.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customThe solvent is evaporated
  3. dissolutionthe residue dissolved in 200 ml of water
  4. filtrationThe resulting crystals are filtered off
  5. washwashed with water
  6. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-802c692a73974b16a32889889838c201
Source dataset
uspto-grants-1997_10
Patent number
US05677303

Reaction notes

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