Hydrochloric Acid → 2-(4-Fluorophenethyl)-5-hydroxybenzoic acid

HRID 1251892Notes

Reaction equation

HRID 1251892 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][C:9]=2[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.Cl>>[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:9]=2[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 18324379Methyl 2-(4-fluorophenethyl)-5-methoxybenzoate

Product 1

HCID 183245242-(4-Fluorophenethyl)-5-hydroxybenzoic acidYield 98.5%

Procedure

Methyl 2-(4-fluorophenethyl)-5-methoxybenzoate (33.8 g, 117 mmol) and pyridine hydrochloride (170 g) were heated at 220° C. for 2 hours. The black reaction mixture was cooled, poured into 2N HCl (1 L), and the pale-brown solid extracted with ethyl acetate (2×450 ml). The extracts were washed with 2N HCl (500 ml), brine (200 ml), dried (MgSO4) and evaporated to give 2-(4-fluorophenethyl)-5-hydroxy benzoic acid (30 g, quantitative).

Workup

  1. customThe black reaction mixture
  2. temperaturewas cooled
  3. extractionthe pale-brown solid extracted with ethyl acetate (2×450 ml)
  4. washThe extracts were washed with 2N HCl (500 ml), brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-fc6c47f7075649048630444b847e9d35
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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