Hydrochloric Acid → 3-[4-[(3-fluorophenyl)methoxy]phenyl]prop-2-enoic Acid

HRID 2184359Notes

Reaction equation

HRID 2184359 reaction equation
FC1C=C(C=CC=1)C[O:6][C:7](=[O:25])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[CH:12][CH:11]=1.[OH-].[Na+].Cl>C1COCC1>[F:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH:9]=[CH:8][C:7]([OH:25])=[O:6])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69288916HCID 69288916, compound

Product 1

HCID 8776273-[4-[(3-fluorophenyl)methoxy]phenyl]prop-2-enoic AcidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

6.48 g (17 mmol) 3-[4-(3-fluoro-benzyloxy)-phenyl]-acrylic acid 3-fluoro-benzyl ester is dissolved in 100 ml THF and 1.36 g (34 mmol) solid sodium hydroxide is added. The reaction mixture is heated overnight at 50° C., cooled and acidified with 1N hydrochloric acid. The precipitate is filtered off and washed with cold water to give 4.43 g (96%) of a colorless solid. MS: m/e=271.2 (M−H).

Workup

  1. temperaturecooled
  2. filtrationThe precipitate is filtered off
  3. washwashed with cold water

Sources & evidence

ORD record
ord-7aa3255db1d442c18a7d8bcbf21a7559
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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