Ethanol → HCID 54003979, compound

HRID 1939355Notes

Reaction equation

HRID 1939355 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].II.C(O)C>C1C=CC=CC=1.CCOCC.C(O)(=O)C>[OH:12][C:9]1([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH:8]1[CH3:13]

Participants

8

Reactant 4

HCID 702EthanolHCID 807IodineHCID 60984Methyl bromoacetateHCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 54003979HCID 54003979, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 241BenzeneSolvent2×HCID 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. Coil., 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 8 h. After addition of 30 ml of 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-indanyl)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 8 h
  5. customThe organic layer is separated
  6. extractionthe aqueous layer is extracted twice with ether
  7. washThe combined organic layers are washed thoroughly with water, ammonium hydroxide and water
  8. dry with materialDrying over sodium sulfate, evaporation of solvent in vacuo
  9. customby pumping at 80°

Sources & evidence

ORD record
ord-5e28f59e3d7e480bb0a28c7c27fab3c7
Source dataset
uspto-grants-1997_12
Patent number
US05696159

Reaction notes

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