Pyridinium chloride → HCID 19078924, compound

HRID 963956Notes

Reaction equation

HRID 963956 reaction equation
C[O:2][C:3]1[CH:34]=[CH:33][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[O:17])=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>O>[OH:31][C:28]1[CH:27]=[CH:26][C:25]([O:24][C:21]2[CH:20]=[CH:19][C:18]([C:16]([C:14]([C:11]3[CH:12]=[CH:13][C:8]([O:7][C:6]4[CH:33]=[CH:34][C:3]([OH:2])=[CH:4][CH:5]=4)=[CH:9][CH:10]=3)=[O:15])=[O:17])=[CH:23][CH:22]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 19078923HCID 19078923, compound

Product 1

HCID 19078924HCID 19078924, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
220 °C

Procedure

In a 250 ml round-bottom flask with a stirbar were placed 4,4'-bis(4-methoxyphenoxy)benzil (7.81 g, 20 mmol) and pyridine hydrochloride (13.87 g, 120 mmol). The mixture was heated under nitrogen in a 220° C. oil bath for 45 mins after which time deprotection was complete. The mixture was cooled to 80° C. and diluted to a volume of 250 ml by dropwise addition of water. The crude product was isolated by suction filtration, washed with water and then recrystallized from acetic acid to give the product (6.91 g, 81%). (mp=220°-221° C.).

Workup

  1. customIn a 250 ml round-bottom flask with a stirbar were placed
  2. temperatureThe mixture was cooled to 80° C.
  3. customThe crude product was isolated by suction filtration
  4. washwashed with water
  5. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-26fe8bdc5fd1497fb48fe18dcc521b5a
Source dataset
uspto-grants-1998_06
Patent number
US05767014

Reaction notes

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