Benzoyl chloride → 2-(2-Hydroxy-4-isopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-2-yl benzoate

HRID 527119Notes

Reaction equation

HRID 527119 reaction equation
[OH:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][C:14]=2[OH:22])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.CC(NP(OC1C=CC(Cl)=CC=1Cl)(OC)=S)C>[C:23]([O:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:20])[CH3:21])=[CH:15][C:14]=2[OH:22])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 30544341H-Indene-1,3(2H)-dione, 2-hydroxy-2-(2-hydroxy-4-(1-methylethyl)phenyl)-

Product 1

HCID 714766762-(2-Hydroxy-4-isopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-2-yl benzoateYield 60%

Reagents, catalysts & solvents 2

HCID 9299ZytronCatalystHCID 6344DichloromethaneSolvent

Procedure

2-hydroxy-2-(2-hydroxy-4-isopropyl-phenyl)-indan-1,3-dione (1.00 g, 3.37 mmol) was completely dissolved in anhydrous methylene chloride (20 ml). This solution was added with benzoyl chloride (0.94 g, 6.74 mmol), triethylamine (0.41 g, 4.04 mmol), and DMPA (0.01 g), followed by heating 24 hrs under reflux. After the reaction mixture was concentrated, extracted with dichloromethane, and the organic layer was concentrated and purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (0.81 g, 14%).

Workup

  1. temperatureby heating 24 hrs
  2. temperatureunder reflux
  3. concentrationAfter the reaction mixture was concentrated
  4. extractionextracted with dichloromethane
  5. concentrationthe organic layer was concentrated
  6. custompurified

Sources & evidence

ORD record
ord-615bee9a0f734bd7bbb05fff6487ce3d
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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