Potassium Hydroxide → 3-{4-[(3-Fluorophenyl)methoxy]phenyl}-2-methylprop-2-enoic acid

HRID 2184349Notes

Reaction equation

HRID 2184349 reaction equation
C[O:2][C:3](=[O:22])[C:4]([CH3:21])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[CH:8][CH:7]=1.[OH-].[K+]>CO>[F:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH:5]=[C:4]([CH3:21])[C:3]([OH:22])=[O:2])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69288939HCID 69288939, compound

Product 1

HCID 692894943-{4-[(3-Fluorophenyl)methoxy]phenyl}-2-methylprop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

383 mg (1.28 mmol) of 3-[4-(3-fluoro-benzyloxy)-phenyl]-2-methyl-acrylic acid methyl ester is added to a solution of 143 mg (2.55 mmol) potassium hydroxide in 7 ml methanol. The solution is stirred at 65° C. for about 3 h, evaporated to dryness, treated with aqueous 0.1 molar hydrochloric acid and extracted 3 times with ethyl acetate. Evaporation of the solvent leaves the pure acid. 305 mg (84%) of a colorless solid. MS (neg.ions): m/e=285.0 (M−H).

Workup

  1. customevaporated to dryness
  2. additiontreated with aqueous 0.1 molar hydrochloric acid
  3. extractionextracted 3 times with ethyl acetate
  4. customEvaporation of the solvent
  5. customleaves the pure acid

Sources & evidence

ORD record
ord-00c76d157a27476e87ec5f50645d1e0c
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

Loading…