HCID 13577659, compound → HCID 13577665, compound

HRID 1589214Notes

Reaction equation

HRID 1589214 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:16])=[CH:4][C:3]=1[CH2:17][CH2:18][OH:19]>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:3]([CH2:17][CH2:18][OH:19])=[CH:4][C:5]([Cl:16])=[CH:6][C:7]=1[C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:15]

Participants

4

Reactant 1

HCID 13577659HCID 13577659, compound

Product 1

HCID 13577665HCID 13577665, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

A suspension of 14 g (0.05 mole) of 2-amino-5-chloro-3-[hydroxy(phenyl)methyl]benzene ethanol in 500 ml of benzene was treated with 23 g (0.25 mole) of activated manganese dioxide and brought to reflux in a vessel fitted with a Dean-Stark trap. After 5 hours the hot mixture was filtered through Celite and the benzene stripped to yield a yellow material. This material was recrystallized from ethanol:pet. ether (30:60) to give 10.8 g of the titled compound, m.p. 135°-137° C.

Workup

  1. temperatureto reflux in a vessel
  2. customfitted with a Dean-Stark trap
  3. filtrationAfter 5 hours the hot mixture was filtered through Celite
  4. customto yield a yellow material
  5. customThis material was recrystallized from ethanol:pet. ether (30:60)

Sources & evidence

ORD record
ord-8c723978ff1f4d5690cb01629776abb8
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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