MAGNESIUM SILICATE (synthetic) → [2-Amino-3-(2-hydroxyethyl)phenyl]phenylmethanone

HRID 1589213Notes

Reaction equation

HRID 1589213 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][CH:5]=[CH:4][C:3]=1[CH2:16][CH2:17][OH:18].[O-][Si]([O-])=O.[Mg+2]>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:3]([CH2:16][CH2:17][OH:18])=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:15]

Participants

5

Reactant 2

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 135776612-Amino-3-[hydroxy(phenyl)methyl]benzeneethanol

Product 1

HCID 13577667[2-Amino-3-(2-hydroxyethyl)phenyl]phenylmethanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

A suspension of 7.7 g of 2-amino-3-[hydroxy(phenyl)methyl]benzene ethanol in 250 ml of benzene was treated with 14 g of activated Manganese dioxide and refluxed for 5 hours using a Dean-Stark trap. The hot mixture obtained was then filtered through Celite and the filtrate stripped to yield a dark oil. The oily material was placed on a florisil column and eluted with a benzene-acetone mixture. The isolated product was recrystallized from ethanol-pet. ether (30:60) to give the titled compound as yellow needles, m.p. 107°-108° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe hot mixture obtained
  3. filtrationwas then filtered through Celite
  4. customto yield a dark oil
  5. washeluted with a benzene-acetone mixture
  6. customThe isolated product was recrystallized from ethanol-pet. ether (30:60)

Sources & evidence

ORD record
ord-7526870d24ab42c5a99c455329e7ffc9
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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