Benzene → Ethyl-(1-hydroxy-2-methyl-6-methoxy-indenyl) acetate

HRID 398246Notes

Reaction equation

HRID 398246 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH3:13])[C:9]2=[O:12])=[CH:5][CH:4]=1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C1C=CC=CC=1.II>C(O)(=O)C.C(O)C.CCOCC>[C:16]([O:18][C:19]1[C:20]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:6][CH3:7])[CH:9]([OH:12])[C:8]=1[CH3:13])(=[O:17])[CH3:15]

Participants

8

Reactant 4

HCID 241Benzene2×HCID 807IodineHCID 7748Ethyl bromoacetateHCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 57181931Ethyl-(1-hydroxy-2-methyl-6-methoxy-indenyl) acetate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 13.4 g of 6-methoxy-2-methylindanone and 21 g. of ethyl bromoacetate in 45 ml. benzene is added over a period of five minutes to 21 g. of zinc amalgam (prepared according to Org. Syn. Coll. Vol. 3) in 110 ml. benzene and 40 ml. dry ether. A few cyrstals of iodine are added to start the reaction, and the reaction mixture is maintained at reflux temperature (ca. 65°) with external heating. At three-hour intervals, two batches of 10 g. zinc amalgam and 10 g. bromoester are added and the mixture is then refluxed for 8 hours. After addition of 30 ml. of ethanol and 150 ml. of acetic acid, the mixture is poured into 700 ml. of 50% aqueous acetic acid. The organic layer is separated, and the aqueous layer is extracted twice with ether. The combined organic layers are washed thoroughly with water, ammonium hydroxide and water. Drying over sodium sulfate, evaporation of solvent in vacuo followed by pumping at 80° (bath temperature)(1-2 mm.) gives crude ethyl-(1-hydroxy-2-methyl-6-methoxy-indenyl) acetate (ca. 18 g.).

Workup

  1. customthe reaction
  2. temperaturethe reaction mixture is maintained
  3. temperatureat reflux temperature (ca. 65°) with external heating
  4. waitAt three-hour intervals, two batches of 10 g
  5. temperaturethe mixture is then refluxed for 8 hours
  6. additionAfter addition of 30 ml
  7. customThe organic layer is separated
  8. extractionthe aqueous layer is extracted twice with ether
  9. washThe combined organic layers are washed thoroughly with water, ammonium hydroxide and water
  10. dry with materialDrying over sodium sulfate, evaporation of solvent in vacuo
  11. customby pumping at 80°

Sources & evidence

ORD record
ord-5cc6b67c615a47e589140ab8fb740ff9
Source dataset
uspto-grants-2003_08
Patent number
US06610854B2

Reaction notes

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