Glycol monoethyl ether → HCID 15067094, compound

HRID 1086254Notes

Reaction equation

HRID 1086254 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[OH-].[Na+].[CH2:13]([O:15][CH2:16][CH2:17][OH:18])[CH3:14]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:13]([O:15][CH2:16][CH2:17][O:18][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)[CH3:14]

Participants

6

Reactant 3

HCID 8076Glycol monoethyl etherHCID 14798Sodium HydroxideHCID 792226-Chloronicotinic acid

Product 1

HCID 15067094HCID 15067094, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 13.2 g (84 mmol) of 6-chloronicotinic acid, 21.2 g (0.53 mol) of powdered sodium hydroxide, 9.5 g (0.106 mol) of 2-ethoxyethanol and 2.64 g (8.2 mmol) of tetrabutylammonium bromide in 350 ml of abs. toluene is heated under reflux for 15 hours. The mixture is evaporated to dryness, and 10% strength hydrochloric acid is added to the residue, while cooling, until the mixture has pH 4. The precipitated acid is filtered off with suction.

Workup

  1. temperatureunder reflux for 15 hours
  2. customThe mixture is evaporated to dryness, and 10% strength hydrochloric acid
  3. additionis added to the residue
  4. temperaturewhile cooling, until the mixture
  5. filtrationThe precipitated acid is filtered off with suction

Sources & evidence

ORD record
ord-c79e4cad249446bf9b7cd992c9944a2b
Source dataset
uspto-grants-1991_07
Patent number
US05028617

Reaction notes

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