Sodium Bicarbonate → [4-(Dimethylamino)phenyl](4-hydroxyphenyl)methanone

HRID 1285114Notes

Reaction equation

HRID 1285114 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>Br>[CH3:1][N:2]([CH3:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 2825054Methanone, [4-(dimethylamino)phenyl](4-methoxyphenyl)-

Product 1

HCID 14205141[4-(Dimethylamino)phenyl](4-hydroxyphenyl)methanoneYield 77.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 10.0 g 1-[4-(dimethylamino)phenyl]-1-(4-methoxyphenyl)-methanone in 30 ml 48% hydrobromic acid was heated at reflux for 21 hours. The reaction mixture was poured into aqueous sodium bicarbonate and the precipitate filtered. Recrystallization from 150 ml of methanol gave 7.3 g of white solid, m.p. 199°-200° C.

Workup

  1. temperatureat reflux for 21 hours
  2. filtrationthe precipitate filtered
  3. customRecrystallization from 150 ml of methanol

Sources & evidence

ORD record
ord-1aaa15cf302240d98408003d7af085b3
Source dataset
uspto-grants-1986_01
Patent number
US04565769

Reaction notes

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