Hydrochloric Acid → HCID 23500200, compound

HRID 1250090Notes

Reaction equation

HRID 1250090 reaction equation
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.Cl.N1C=CC=CC=1.Cl>>[OH:11][C:7]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:19])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 11021491HCID 11021491, compound

Product 1

HCID 23500200HCID 23500200, compoundYield 58%

Conditions

Temperature
180 °C

Procedure

3-methoxy-2-phenylbenzoic acid ethyl ester (0.53 g) and pyridine hydrochloride (6 g) were combined under nitrogen, then heated to 180° C. for 1 hour. The melt was poured into dilute aqueous hydrochloric acid and extracted with ethyl acetate. Purification by silica gel chromatography, eluting with hexane/acetone (2:1) with 0.5% acetic acid, gave 3-hydroxy-2-phenylbenzoic acid as a white solid (0.25 g, 58%).

Workup

  1. extractionextracted with ethyl acetate
  2. customPurification by silica gel chromatography
  3. washeluting with hexane/acetone (2:1) with 0.5% acetic acid

Sources & evidence

ORD record
ord-90a05877584449199a38e0fe1102b706
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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