3-Hydroxyacetophenone → HCID 71476534, compound

HRID 527117Notes

Reaction equation

HRID 527117 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]([OH:13])(O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[OH:14][C:15]1[CH:16]=[C:17]([C:21](=[O:23])[CH3:22])[CH:18]=[CH:19][CH:20]=1>C(O)(=O)C.C(Cl)Cl>[C:21]([C:17]1[CH:18]=[CH:19][C:20]([C:9]2([OH:13])[C:10](=[O:11])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7]2=[O:8])=[C:15]([OH:14])[CH:16]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 2

HCID 84873-HydroxyacetophenoneHCID 10236Ninhydrin

Product 1

HCID 71476534HCID 71476534, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ninhydrin (1.00 g, 5.61 mmol) in acetic acid (20 ml) was added 1-(3-hydroxy-phenyl)-ethanone (0.76 g, 5.61 mmol), followed by heating for 3 hrs at 110° C. The reaction mixture was diluted with methylene chloride, extracted with 2N NaOH aqueous solution, and the concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:2) to afford the title compound (White, 1.32 g, 79%).

Workup

  1. extractionextracted with 2N NaOH aqueous solution
  2. customthe concentrated organic layer was purified

Sources & evidence

ORD record
ord-40a20368ba9247e79a2cf5b6631065c0
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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