Ninhydrin → 1,3-Indandione, 2-(3,5-dimethyl-p-hydroxyphenyl)-2-hydroxy-

HRID 527121Notes

Reaction equation

HRID 527121 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].[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[OH:22]>C(O)(=O)C>[OH:13][C:9]1([C:19]2[CH:18]=[C:17]([CH3:21])[C:16]([OH:22])=[C:15]([CH3:14])[CH:20]=2)[C:10](=[O:11])[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7]1=[O:8]

Participants

4

Reactant 2

HCID 10236NinhydrinHCID 113352,6-Dimethylphenol

Product 1

HCID 30544231,3-Indandione, 2-(3,5-dimethyl-p-hydroxyphenyl)-2-hydroxy-Yield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ninhydrin (1.00 g, 5.61 mmol) and 2,6-dimethylphenol (686 mg, 5.61 mmol) was dissolved in acetic acid (15 ml), and this solution was heated for 13 hrs. The reaction mixture was concentrated, and extracted with dichloromethane, and then concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:2) to afford the title compound (0.31 g, 20%).

Workup

  1. temperaturethis solution was heated for 13 hrs
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with dichloromethane
  4. customconcentrated organic layer was purified

Sources & evidence

ORD record
ord-15ffb7cc92bb43df930f4f80ec36ab5f
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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