Hydrochloric Acid → 3-Pyridinecarboxylic acid, 2-phenoxy-

HRID 1731740Notes

Reaction equation

HRID 1731740 reaction equation
[Na].[C:2]1([OH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].Cl>CO>[O:8]([C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 762582-Chloronicotinic acidHCID 5360545Sodium

Product 1

HCID 1234503-Pyridinecarboxylic acid, 2-phenoxy-Yield 86.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

55.2 g of sodium was added portionwise to 1500 ml of anhydrous methanol. When the reaction was complete 120 g of phenol and 200 g of 2-chloronicotinic acid were added, and the mixture was heated until completely solubilized. The methanol was removed by distillation, and the residue heated to 180°-200° C. for 5 minutes. The molten mass was cooled to about 100° C., and water was added slowly. The solution obtained was acidified with hydrochloric acid. After standing for about 16 hours, the solid obtained was filtered and dried, giving 237.4 g of 2-phenoxynicotinic acid, as white crystals, m.p. 179-181° C. (Kofler micro hot-stage); neutralization equivalent: 215.20 (calculated 216.55).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. customThe methanol was removed by distillation
  4. temperaturethe residue heated to 180°-200° C. for 5 minutes
  5. additionwater was added slowly
  6. customThe solution obtained
  7. customthe solid obtained
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-389f6c21789947dcab770ac874f0ceeb
Source dataset
uspto-grants-1986_11
Patent number
US04623648

Reaction notes

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