2-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-one → HCID 53700019, compound

HRID 262438Notes

Reaction equation

HRID 262438 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][OH:13])[CH:6]=1)=[O:4].[CH3:14][N:15]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:16]1C=C[CH:19]=[C:18]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=1>CC(=O)CC>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:22]([CH:18]([CH3:19])[CH2:17][CH2:16][N:15]([CH3:14])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][C:7]=1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 113340552-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-oneHCID 21318919HCID 21318919, compound

Product 1

HCID 53700019HCID 53700019, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone (9.1 g) and N-methyl-N-phenyl-N'-(phenylmethyl)-1,3-benzenediamine (16.6 g) in butanone (200 ml) was heated under reflux for 4 hours. The mixture was cooled at 0° and the amine hydrobromide was filtered off. The filtrate was evaporated and a solution of the residue in 2 N hydrochloric acid (200 ml) was extracted with ethyl acetate. The acidic solution was basified with solid sodium bicarbonate and then extracted with ethyl acetate. The solvents were evaporated to give a brown gum (10.7 g). The crude product in ethyl acetate was filtered through a column of silica (100 g) to yield a light brown gum (7.9 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe mixture was cooled at 0°
  3. filtrationthe amine hydrobromide was filtered off
  4. customThe filtrate was evaporated
  5. extractiona solution of the residue in 2 N hydrochloric acid (200 ml) was extracted with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. customThe solvents were evaporated

Sources & evidence

ORD record
ord-a5cb4cefb5684a48977f70234638762b
Source dataset
uspto-grants-1979_05
Patent number
US04154761

Reaction notes

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