Methanol → 2-Isopropyl-4-(4-fluorophenyl)-3-butenoic acid

HRID 1395609Notes

Reaction equation

HRID 1395609 reaction equation
[CH:1]([CH:4]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]([O:7]CC)=[O:6])([CH3:3])[CH3:2].[OH-].[K+].CO>O>[CH:1]([CH:4]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 53866659Ethyl 2-isopropyl-4-(4-fluorophenyl)-3-butenoate

Product 1

HCID 538855142-Isopropyl-4-(4-fluorophenyl)-3-butenoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the above ester (0.46 g), potassium hydroxide (2.5 mmol), 3 ml methanol and 0.5 ml water is stirred at about 45° overnight. Methanol is removed by evaporation and then 5% NaOH-ether is added. After adjusting to about pH 3 by addition of dilute HCl, the mixture is extracted with ether. The ether phase is washed with water and brine, dried over sodium sulfate, and solvent evaporated to yield 2-isopropyl-4-(4-fluorophenyl)-3-butenoic acid.

Workup

  1. customMethanol is removed by evaporation
  2. addition5% NaOH-ether is added
  3. additionAfter adjusting to about pH 3 by addition of dilute HCl
  4. extractionthe mixture is extracted with ether
  5. washThe ether phase is washed with water and brine
  6. dry with materialdried over sodium sulfate, and solvent
  7. customevaporated

Sources & evidence

ORD record
ord-245ee3bfa4fb4fcea7eba4eb616a47df
Source dataset
uspto-grants-1980_05
Patent number
US04204071

Reaction notes

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