Ethylene Glycol → HCID 19922448, compound

HRID 1463664Notes

Reaction equation

HRID 1463664 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-methoxybenzeneacetic 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-17af68f427cc410e9f4df32aa1670df8
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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