Hydrochloric Acid → 2-(2-(4-Fluorobenzyl)phenyl)acetic acid

HRID 2378498Notes

Reaction equation

HRID 2378498 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]#N)=[CH:4][CH:3]=1.[OH2:18].S(=O)(=O)(O)[OH:20].Cl>C(O)(=O)C.ClCCl>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]([OH:20])=[O:18])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 11206883[2-(4-Fluoro-benzyl)-phenyl]-acetonitrile

Product 1

HCID 112302882-(2-(4-Fluorobenzyl)phenyl)acetic acidYield 74%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

[2-(4-fluoro-benzyl)-phenyl]-acetonitrile is suspended in acetic acid (0.5 L/mol), water (0.3 L/mol) and sulphuric acid (0.35 L/mol). After 5 hours at reflux, the mixture is cooled down, water (1.2 L/mol) and dichloromethane (0.3 L/mol) are added. The organic extract is washed with water (1.3 L/mol) and sodium hydroxide 50% (0.15 L/mol). After stirring for 20 min., the aqueous layer is separated and washed with CH2Cl2 (0.1 L/mol) which is discarded. The aqueous layer is acidified with concentrated hydrochloric acid (2 eq.). The mixture is stirred during 3 hours, the precipitate is then filtered off and washed with water (0.1 L/mol). Yield: 74%.

Workup

  1. temperatureAfter 5 hours at reflux
  2. temperaturethe mixture is cooled down
  3. extractionThe organic extract
  4. washis washed with water (1.3 L/mol) and sodium hydroxide 50% (0.15 L/mol)
  5. customthe aqueous layer is separated
  6. washwashed with CH2Cl2 (0.1 L/mol) which
  7. stirringThe mixture is stirred during 3 hours
  8. filtrationthe precipitate is then filtered off
  9. washwashed with water (0.1 L/mol)

Sources & evidence

ORD record
ord-6f877b3afe784d1a8d741557020d2af1
Source dataset
uspto-grants-2008_12
Patent number
US07470809B2

Reaction notes

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