Sodium Hydroxide → 5-Fluoronaphthalene-1-acetic acid

HRID 331249Notes

Reaction equation

HRID 331249 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:12][C:13]([O:15]CC)=[O:14].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86641635Ethyl (5-fluoronaphthalen-1-yl)acetate

Product 1

HCID 687023935-Fluoronaphthalene-1-acetic acidYield 82.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (5-fluoronaphthalen-1-yl)acetate (5.96 g) in ethanol (50 mL) was added 1N sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, the obtained residue was poured into water, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 1N hydrochloric acid, and extracted with chloroform, and the extract was washed with water and saturated brine, dried is over magnesium sulfate, and concentrated under reduced pressure to give (5-fluoronaphthalen-1-yl)acetic acid (4.34 g). The title compound was obtained according to the method of Example 103 and using (5-fluoronaphthalen-1-yl)acetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe obtained residue was poured into water
  3. washthe mixture was washed with ethyl acetate
  4. extractionextracted with chloroform
  5. washthe extract was washed with water and saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87a05bb0138248d6b1341826929b36c7
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

Loading…