Sodium Hydroxide → HCID 22504600, compound

HRID 1368940Notes

Reaction equation

HRID 1368940 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1.Cl.[CH3:21][N:22]([CH2:24][CH2:25]Cl)[CH3:23]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:25][CH2:24][N:22]([CH3:23])[CH3:21])=[CH:17][CH:18]=2)=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2726363HCID 2726363, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 22504600HCID 22504600, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

10% Aqueous sodium hydroxide is added to the mixture containing 2-(4-chlorophenyl)-1-(4-hydroxyphenyl)ethanone (6.0 g, 0.024 mol), TBABr (0.9 g) in toluene (60 ml) at 60° C. The mixture is stirred for 30 min. N,N-Dimethylaminoethyl chloride hydrochloride (3.6 g, 0.025 mol) is added and stirring is continued at 70-75° C. for 3 h. The layers are separated and the aqueous phase is extracted with toluene. The combined toluene phases are evaporated to give the product (1.85 g, 24%).

Workup

  1. stirringstirring
  2. waitis continued at 70-75° C. for 3 h
  3. customThe layers are separated
  4. extractionthe aqueous phase is extracted with toluene
  5. customThe combined toluene phases are evaporated

Sources & evidence

ORD record
ord-bf655120a6084593bf10a6ad320ac2cb
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

Loading…