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

HRID 1609625Notes

Reaction equation

HRID 1609625 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][CH3:19])=[O:17].C1C=CC=CC=1.II>C(O)(=O)C.C(O)C.CCOCC>[CH3:19][O:18][C:16](=[O:17])[CH2:15][C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:9]([OH:12])[C:8]=1[CH3:13]

Participants

8

Reactant 4

HCID 241Benzene2×HCID 807IodineHCID 60984Methyl bromoacetateHCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 131718936Methyl(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 19.3 g. of methyl bromoacetate in 45 ml. benzene is added over a period of 5 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 crystals 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 eight hours. After addition of 30 ml. ethanol and 150 ml. of acetic acid, the mixture is poured into 700 ml. of 1:1 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 temp.) (1-2 mm.) gives crude methyl(1-hydroxy-2-methyl-6-methoxy-indenyl)acetate.

Workup

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

Sources & evidence

ORD record
ord-6de360e13fd94a7db2f7db0438d43f8f
Source dataset
uspto-grants-1995_03
Patent number
US05401774

Reaction notes

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