HCID 13577664, compound → HCID 13577670, compound

HRID 1589216Notes

Reaction equation

HRID 1589216 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:17][CH2:18][OH:19]>[O-2].[O-2].[Mn+4].C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([CH2:17][CH2:18][OH:19])=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([Br:16])=[CH:14][CH:15]=1)=[O:9]

Participants

4

Reactant 1

HCID 13577664HCID 13577664, compound

Product 1

HCID 13577670HCID 13577670, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 5.3 g (0.016 mole) of 2-amino-3-[(4-bromophenyl)hydroxymethyl]benzeneethanol, 7.1 g (0.08 mole) of manganese dioxide and 250 ml of benzene was heated at reflux for 20 hr. utilizing a Dean-Stark trap for water removal. The mixture was filtered through celite and the filtrate was concentrated under reduced pressure to give 4.8 g of brown gum as residue. The residue was purified by column chromatography on 100 g of silica gel and the product was eluted with 15% ethyl acetate in benzene. The fractions containing the title compound were combined and concentrated under reduced pressure to give a solid residue. The solid was recrystallized from cyclohexane benzene to give 1.6 g (30%) of the titled compound as orange flakes,

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. customutilizing a Dean-Stark trap for water removal
  4. filtrationThe mixture was filtered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c16fc4d9ccc4941869813ab0d91272f
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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