4'-Hydroxyacetophenone → HCID 12202647, compound

HRID 1579386Notes

Reaction equation

HRID 1579386 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.Cl[C:13]1[N:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>CO>[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][C:13]2[N:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[CH:4][CH:5]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 762582-Chloronicotinic acidHCID 5360545Sodium

Product 1

HCID 12202647HCID 12202647, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.03 g of metallic sodium in 27 ml of methanol are added 10 g of p-hydroxyacetophenone and 3.36 g of 2-chloronicotinic acid. The methanol is removed by raising the temperature. The mixture is allowed to stand at 160°-170°C for 2.5 hours. Water is added to the reaction mixture, and the precipitate (excess p-hydroxyacetophenone) is removed by filtration. The filtrate is acidified with hydrochloric acid to yield crystals. The crystals are filtered off, washed with water and chloroform to give 2-(p-acetylphenoxy)nicotinic acid melting at 184°-186°C.

Workup

  1. customThe methanol is removed
  2. temperatureby raising the temperature
  3. additionWater is added to the reaction mixture
  4. customthe precipitate (excess p-hydroxyacetophenone) is removed by filtration
  5. customto yield crystals
  6. filtrationThe crystals are filtered off
  7. washwashed with water and chloroform

Sources & evidence

ORD record
ord-18436034f01345648591f6a43dedee88
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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