Water → HCID 15475793, compound

HRID 1285115Notes

Reaction equation

HRID 1285115 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+].Br[CH2:22][CH2:23][OH:24].O>CN(C)C=O.C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:22][CH2:23][OH:24])=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 14798Sodium Hydroxide2×HCID 14205141[4-(Dimethylamino)phenyl](4-hydroxyphenyl)methanone

Product 1

HCID 15475793HCID 15475793, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 12.0 g of 1-[4-(dimethylamino)phenyl]-1-[4-hydroxyphenyl)-methanone and 2.2 g sodium hydroxide in 120 ml dimethylformamide was heated at 90° C. until all the sodium hydroxide had dissolved. 6.9 g 2-bromoethanol was added and the reaction heated at about 105° C. for 24 hours. The reaction mixture was poured into water and the product isolated by extraction with methylene chloride to yield 7.7 g, m.p. 142°-143° C., λmax (chloroform) 348 nm (ε=26,400), 271 nm (ε=12,500), 255 nm (ε=11,900 nm).

Workup

  1. dissolutionhad dissolved

Sources & evidence

ORD record
ord-4fa73bb707974d43886ab509f0f09540
Source dataset
uspto-grants-1986_01
Patent number
US04565769

Reaction notes

Loading…