HCID 13577662, compound → HCID 13577668, compound

HRID 1589215Notes

Reaction equation

HRID 1589215 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl: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]([Cl:16])=[CH:14][CH:15]=1)=[O:9]

Participants

4

Reactant 1

HCID 13577662HCID 13577662, compound

Product 1

HCID 13577668HCID 13577668, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 6.0 g (0.022 mole) of 2-amino-3-[(4-chlorophenyl)hydroxymethyl]benzene ethanol, 8.7 g (0.10 mole) of activated manganese dioxide and 250 ml of benzene was heated at reflux utilizing a Dean-Stark trap for 5 hours. The hot mixture obtained was filtered through Celite and the filtrate was concentrated to give a solid residue. This residue was recrystallized successively from carbon tetrachloride, cyclohexane and benzene, and 2-propanol to yield 2.9 g (48%) of the titled compound as a yellow solid,

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customfor 5 hours
  4. customThe hot mixture obtained
  5. filtrationwas filtered through Celite
  6. concentrationthe filtrate was concentrated
  7. customto give a solid residue
  8. customThis residue was recrystallized successively from carbon tetrachloride, cyclohexane and benzene, and 2-propanol

Sources & evidence

ORD record
ord-a3d463a5830644f2aa4ccc1577bea653
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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