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

HRID 1252620Notes

Reaction equation

HRID 1252620 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.O.[OH-].[K+].Cl>O1CCCC1>[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 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 14182499Benzyl 4,5-bis(benzyloxy)pyridine-2-carboxylate

Product 1

HCID 141825074,5-bis(phenylmethoxy)-2-Pyridinecarboxylic acidYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11.8 g (28 mmol) of 4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid, phenylmethyl ester in 115 ml of tetrahydrofuran was added 16 ml of water and 35 ml of 1N potassium hydroxide. After stirring overnight at room temperature, 115 ml of water was added and the pH was adjusted to 2.5 with 1N hydrochloric acid. The acid was filtered off, washed with water and dried in vacuo, yielding 8.6 g of the title compound, melting point 203.6° C.

Workup

  1. filtrationThe acid was filtered off
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c797349715bb466c869c224aee970d03
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

Loading…