Dimethyl Carbonate → Methyl 7-cyclohexyl-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate

HRID 861867Notes

Reaction equation

HRID 861867 reaction equation
[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].[C:21](=O)([O:24]C)[O:22][CH3:23]>>[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH:13]([C:21]([O:22][CH3:23])=[O:24])[C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 15324703HCID 15324703, compound

Product 1

HCID 19700499Methyl 7-cyclohexyl-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylateYield 74%

Procedure

A mixture of 7-cyclohexyl-1-tetralone (9.4 g), sodium methoxide (8.9 g) and dimethyl carbonate (65 ml) was refluxed for 30 minutes in a nitrogen gas stream. After the reaction mixture was cooled, the resulting crystals were collected by filtration and suspended in ethyl acetate (250 ml), followed by addition of 6N HCl (50 ml). The organic layer was collected, while the aqueous layer was extracted with ethyl acetate. The extract was combined with the organic layer, successively washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off, to yield methyl 7-cyclohexyl-1-tetralone-2-carboxylate (8.6 g, 74%) as an oil.

Workup

  1. temperaturewas refluxed for 30 minutes in a nitrogen gas stream
  2. temperatureAfter the reaction mixture was cooled
  3. filtrationthe resulting crystals were collected by filtration
  4. additionfollowed by addition of 6N HCl (50 ml)
  5. customThe organic layer was collected, while the aqueous layer
  6. extractionwas extracted with ethyl acetate
  7. washsuccessively washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customafter which the solvent was evaporated off

Sources & evidence

ORD record
ord-ac582ceb4e8146d48ee8583c987008d4
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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