Diethyl Ether → HCID 14457388, compound

HRID 1862035Notes

Reaction equation

HRID 1862035 reaction equation
[C:1]([O:13]C)(=O)[C:2]1[C:3](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:4]([O:6]C)=O.C[O-].[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=1.CCOCC>O1CCCC1.O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:26]2[C:1](=[O:13])[C:2]3[C:3](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:4]2=[O:6])=[O:27])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7467P-ChloroacetophenoneHCID 8554Dimethyl PhthalateHCID 10942334Sodium Methoxide

Product 1

HCID 14457388HCID 14457388, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

Dimethyl phthalate (15.0 g) in tetrahydrofuran (100 ml) was added to a stirred suspension of sodium methoxide (8.31 g) in tetrahydrofuran (60 ml) followed by 4′-chloroacetophenone (11.8 g) in tetrahydrofuran (100 ml) at 20° C. under nitrogen. The mixture was then boiled under reflux for 18 hours then cooled to 20° C. and poured into ether (250 ml) and water (250 ml). The aqueous layer was separated and the organic layer was washed with water (3×75 ml). The combined aqueous extract and washings were acidified with concentrated hydrochloric acid and the solid which precipitated was collected by filtration. The filtrate was extracted with dichloromethane, dried and evaporated. The residue was recrystallized from ethanol to give 2-(4-chlorobenzoyl)-indan-1,3-dione.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with water (3×75 ml)
  4. extractionThe combined aqueous extract
  5. customthe solid which precipitated
  6. filtrationwas collected by filtration
  7. extractionThe filtrate was extracted with dichloromethane
  8. customdried
  9. customevaporated
  10. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-71aaf565036445599b0a29d94fd1e9a1
Source dataset
uspto-grants-2003_03
Patent number
US06534655B1

Reaction notes

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