Hydrochloric Acid → 4,5-bis(phenylmethoxy)-2-Pyridinecarboxylic acid

HRID 4109Notes

Reaction equation

HRID 4109 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([C:23]([O:25]CC3C=CC=CC=3)=[O:24])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl>O1CCCC1.O>[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][N:12]=[C:11]([C:23]([OH:25])=[O:24])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14182499Benzyl 4,5-bis(benzyloxy)pyridine-2-carboxylate

Product 1

HCID 141825074,5-bis(phenylmethoxy)-2-Pyridinecarboxylic acidYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid, phenylmethyl ester (1.60 g, 3.76 mmole) in 15 ml of tetrahydrofuran and 2.2 ml of water was added 4 ml of 1N aqueous potassium hydroxide. The mixture was stirred at room temperature overnight. Water (15 ml) was added and 1N hydrochloric acid was added slowly with stirring while monitoring the pH. The pH of the mixture fell steadily to ca. 6.2 whereupon a large amount of solid began to separate and no further decrease in the pH was noted. Continued addition of hydrochloric acid eventually effected a sudden drop in pH to 3.2 and the addition was stopped. The solid was filtered and washed well with water, then ether, and dried in vacuo to afford 1.197 g of the title compound as a white waxy solid.

Workup

  1. stirringwith stirring
  2. customto separate
  3. additionContinued addition of hydrochloric acid
  4. additionthe addition
  5. filtrationThe solid was filtered
  6. washwashed well with water
  7. dry with materialether, and dried in vacuo

Sources & evidence

ORD record
ord-1ae072769e534869ae592e459a10025e
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Reaction notes

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