Sodium Hydroxide → HCID 21511442, compound

HRID 1576577Notes

Reaction equation

HRID 1576577 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13](C)([C:19]([O-])=O)[C:14]([O:16]CC)=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:19])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21511462HCID 21511462, compound

Product 1

HCID 21511442HCID 21511442, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
220 °C

Procedure

Ethyl 2-[4-(4-fluorophenoxy)phenyl]-2-methylmalonate (19.6 g.) was refluxed for 1 hour with a mixture of 2.5N aqueous sodium hydroxide (114 ml.) and ethanol (57 ml.). After cooling and acidification with 5N hydrochloric acid, the resulting oil was extracted into ether. The extract was washed with water, dried and the ether distilled. The residue of crude 2-[4-(4-fluorophenoxy)phenyl]-2-methylmalonic acid was decarboxylated by heating for 20 minutes at 220°C. The product was recrystallised several times from benzene/petroleum ether b.p. 62°-68°C. to give 2-[4-(4-fluorophenoxy)phenyl]propionic acid, m.p. 84°-86°C.

Workup

  1. temperatureAfter cooling
  2. extractionacidification with 5N hydrochloric acid, the resulting oil was extracted into ether
  3. washThe extract was washed with water
  4. customdried
  5. distillationthe ether distilled
  6. customThe product was recrystallised several times from benzene/petroleum ether b.p. 62°-68°C.

Sources & evidence

ORD record
ord-1abff8f5a61e47599220edbd3a3de699
Source dataset
uspto-grants-1976_09
Patent number
US03981905

Reaction notes

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