Hydrochloric Acid → HCID 22314484, compound

HRID 966083Notes

Reaction equation

HRID 966083 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#N.[OH-:19].[Na+].Cl.[OH2:22]>>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]([OH:22])=[O:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 22314487HCID 22314487, compound

Product 1

HCID 22314484HCID 22314484, compoundYield 53%

Procedure

A suspension of 2-fluoro-4-(3-fluoro-benzyloxy)-benzonitrile (24.5 g, 100 mmol) and sodium hydroxide (30 g, 750 mmol) in water (300 mL) was heated under reflux for 16 h. After cooling to room temperature the suspension was acidified to pH 2 with concentrated hydrochloric acid. The resulting mixture was diluted with water (100 mL) and extracted with ether (3×400 mL). The combined organic extracts were then washed with water and brine and then dried over sodium sulfate. Filtration and half evaporation of the filtrate resulted in the formation of a white precipitate which was filtered off to afford the title compound (14 g, 53%) as white crystals after recrystallisation from cyclohexane: ethyl acetate. MS: m/e=263.1 (M−H−)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. extractionextracted with ether (3×400 mL)
  4. washThe combined organic extracts were then washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and half evaporation of the filtrate
  7. customresulted in the formation of a white precipitate which
  8. filtrationwas filtered off

Sources & evidence

ORD record
ord-ba53fd82a31a48f7822ebe862dd8aed1
Source dataset
uspto-grants-2005_10
Patent number
US06951884B2

Reaction notes

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