Water → 2-methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one

HRID 2089085Notes

Reaction equation

HRID 2089085 reaction equation
[CH:1]1[CH2:2][C:3](=O)[CH:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.[OH2:12]>>[CH3:4][CH:5]1[C:10](=[O:12])[C:2]2=[CH:1][C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[CH:4]=[C:3]2[CH2:6]1

Participants

3

Reactant 2

HCID 962WaterHCID 20192716Naphthalen-3-one

Product 1

HCID 224992222-methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one

Procedure

The reaction is diluted with water and extracted with dichloromethane. After drying (Na2SO4) the solvent is removed to give an oil. The product is purified by chromatography (silica, ethyl acetate/hexane) to give a geometrical mixture of isomers containing 2-Methyl-1,2,6,7,8,9-hexahydro-cyclopenta[.a.]naphthalen-3-one and the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialAfter drying (Na2SO4) the solvent
  3. customis removed
  4. customto give an oil
  5. customThe product is purified by chromatography (silica, ethyl acetate/hexane)
  6. customto give
  7. additiona geometrical mixture of isomers
  8. additioncontaining 2-Methyl-1,2,6,7,8,9-hexahydro-cyclopenta[.a

Sources & evidence

ORD record
ord-f6363a541244451d9f99629d4227ec76
Source dataset
uspto-grants-2013_05
Patent number
US08436017B2

Reaction notes

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