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

HRID 276933Notes

Reaction equation

HRID 276933 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 wasted 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. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-acb542a6e6d94a8a91e578c92418653a
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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