Water → 2-Fluoro-4-pentylbenzoic acid

HRID 466500Notes

Reaction equation

HRID 466500 reaction equation
S(=O)(=O)(O)[OH:2].[OH2:6].[F:7][C:8]1[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:13]=[CH:12][C:9]=1[C:10]#N>C(O)(=O)C>[F:7][C:8]1[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:13]=[CH:12][C:9]=1[C:10]([OH:2])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 19010185HCID 19010185, compound

Product 1

HCID 190101812-Fluoro-4-pentylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of concentrated sulphuric acid (150 ml) and water (150 ml) was added dropwise to a stirred solution of compound 21 (15.0 g, 0.078 mol) in glacial acetic acid (300 ml). The stirred mixture was heated under reflux for 48 h, cooled in a refrigerator overnight and the product was filtered off. The product was dissolved in ether, extracted into 10% sodium hydroxide, which was then acidified with 36% hydrochloric acid, washed with ether (twice), and the combined ethereal phases were washed with water and dried (MgSO4). The solvent was removed in vacuo to give a brown crystalline solid.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 48 h
  3. temperaturecooled in a refrigerator overnight
  4. filtrationthe product was filtered off
  5. dissolutionThe product was dissolved in ether
  6. extractionextracted into 10% sodium hydroxide, which
  7. washwashed with ether (twice), and the combined ethereal phases
  8. washwere washed with water
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed in vacuo
  11. customto give a brown crystalline solid

Sources & evidence

ORD record
ord-cb7d8e0d8b694f709bf72d5b6bacce8b
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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