Hydrochloric Acid → HCID 20298531, compound

HRID 1389146Notes

Reaction equation

HRID 1389146 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH:14]([CH3:21])[CH2:15][C:16]([O:18]CC)=[O:17])[CH:3]=1.[OH-].[Na+].O.Cl>CO>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH:14]([CH3:21])[CH2:15][C:16]([OH:18])=[O:17])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 20298527HCID 20298527, compound

Product 1

HCID 20298531HCID 20298531, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester (9 g) was dissolved in methanol (180 ml) and 10% aqueous sodium hydroxide solution (90 ml) was added. The solution was heated under reflux for 2 hours. It was then poured into water (270 ml) and the suspension was acidified with dilute hydrochloric acid. The precipitate produced was extracted into ethyl acetate. The organic solution was dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure to give 3-(4-fluoro-6-methoxy-2-naphthyl)butanoic acid as an oil which crystallised on standing (12.4 g., >100%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 hours
  3. customThe precipitate produced
  4. extractionwas extracted into ethyl acetate
  5. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-029f5eada9db4fdb87695eb6f462da18
Source dataset
uspto-grants-1981_01
Patent number
US04243682

Reaction notes

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