Ethylene Glycol → HCID 19922448, compound

HRID 1681766Notes

Reaction equation

HRID 1681766 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([CH2:19][C:20]2[CH:25]=[CH:24]N=[CH:22][CH:21]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[C:9]#N)=[CH:3][CH:2]=1.[OH-:26].[K+].[Cl-].[NH4+:29].C(O)C[OH:32]>O>[N:29]1[CH:24]=[CH:25][C:20]([CH2:19][C:8]([CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[C:9]([OH:32])=[O:26])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 19922432HCID 19922432, compound

Product 1

HCID 19922448HCID 19922448, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of α,α-Bis(4-pyridinylmethyl)-2-methoxybenzeneacetonitrile (14.36 g, 43.6 mmol) in ethylene glycol (100 ml), was added KOH (40 ml of a saturated solution) and the mixture was heated at 120°-130° under nitrogen for 20 h. The solution was cooled to room temperature, diluted with 200 ml water, and neutralized with aqueous ammonium chloride to about pH 7. The mixture was extracted with chloroform: isopropanol (4:1) until complete by TLC. the combined extracts were washed with brine, dried over sodium sulfate, and evaporated (rotary evaporator). The solid was dried in a vacuum oven at 50° and 5 torr to give 7.7 g, 22 mmol, 50% yield of α,α-bis(4-pyridinylmethyl)-2-methoxybenzene-acetic acid as a white powder.

Workup

  1. temperaturethe mixture was heated at 120°-130° under nitrogen for 20 h
  2. extractionThe mixture was extracted with chloroform: isopropanol (4:1) until complete by TLC
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. custom(rotary evaporator)
  7. customThe solid was dried in a vacuum oven at 50°

Sources & evidence

ORD record
ord-2d451c81503c4cca9a79c76495219c80
Source dataset
uspto-grants-1992_12
Patent number
US05173489

Reaction notes

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