Hydrochloric Acid → 2-[2-(4-Fluorophenyl)ethyl]benzoic acid

HRID 8399Notes

Reaction equation

HRID 8399 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#N)=[CH:4][CH:3]=1.[OH-:18].[Na+].[OH2:20].Cl>C(O)CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]([OH:20])=[O:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22015785HCID 22015785, compound

Product 1

HCID 220158012-[2-(4-Fluorophenyl)ethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 2-[2-(4-fluorophenyl)ethyl]benzonitrile (8.03 g, 35.6 mmol, 1 equiv) and aq. NaOH (10N; 16 mL, 160 mmol, 4.5 equiv) in ethylene glycol (100 mL) was heated to 190 C for 69 h. After allowing the reaction mixture to cool, H2O (300 mL) was added, followed by 12N HCl (16 mL). This mixture was extracted with CHCl3 (1×100 mL) and the organic layer was then washed with H2O (2×50 mL). The organic layer was dried (anh. Na2SO4) and rotary evaporated (90° C.). This provided 7.44 g (85.4%) of a light-yellow solid.

Workup

  1. temperaturewas heated to 190 C for 69 h
  2. temperatureto cool
  3. extractionThis mixture was extracted with CHCl3 (1×100 mL)
  4. washthe organic layer was then washed with H2O (2×50 mL)
  5. dry with materialThe organic layer was dried (anh. Na2SO4)
  6. customrotary evaporated (90° C.)

Sources & evidence

ORD record
ord-4debe123c0e647088929ba120d5af46f
Source dataset
uspto-grants-2006_08
Patent number
US07087765B2

Reaction notes

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