Potassium Carbonate → 1-Methoxycarbonylmethoxy-5-oxo-5,6,7,8-tetrahydronaphthalene

HRID 965342Notes

Reaction equation

HRID 965342 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>C(#N)C>[CH3:24][O:23][C:21]([CH2:20][O:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 141811861-Methoxycarbonylmethoxy-5-oxo-5,6,7,8-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-hydroxy-5-oxo-5,6,7,8-tetrahydronaphthalene (10 g), potassium carbonate (9.4 g), methyl bromoacetate (6.2 ml) in acetonitrile (250 ml) was refluxed with stirring for 3.5 hours. The mixture was filtered off and the filtrate was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The separated organic layer was washed with 1N-hydrochloric acid, 1N-sodium hydroxide, brine, dried over magnesium sulfate and evaporated in vacuo. The residue was suspended in n-hexane and then the solid was collected by filtration to give 1-methoxycarbonylmethoxy-5-oxo-5,6,7,8-tetrahydronaphthalene (13.90 g).

Workup

  1. temperaturewas refluxed
  2. filtrationThe mixture was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe separated organic layer was washed with 1N-hydrochloric acid, 1N-sodium hydroxide, brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-39536d0d92b546fca35d7e4f34db5d17
Source dataset
uspto-grants-1998_06
Patent number
US05773530

Reaction notes

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