HCID 54058339, compound → HCID 53705215, compound

HRID 1284342Notes

Reaction equation

HRID 1284342 reaction equation
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[C:11](=[CH:17][C:18]([O:20][CH3:21])=[O:19])[CH2:10][CH2:9]2>C(OCC)C>[CH3:1][C:12]1[C:13]2[C:8](=[CH:7][C:6]([O:5][CH3:4])=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 54058339HCID 54058339, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 53705215HCID 53705215, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

To a mixture of 12 g. of methyl magnesium bromide and 200 ml. of diethyl ether, 25 g. of 6-methoxy-2-(methoxycarbonylmethylene)-1-tetralone are added. The alkylating mixture is refluxed for one hour after it has been allowed to stand for one hour; the mixture is made acidic to litmus by the addition of 1N methanolic HC1, filtered, and evaporated. The residue, containing methyl 1-methyl-6-methoxy-3,4-dihydro-2-naphthylacetate, is added to 1 g. of 10% palladium-on-charcoal and the resulting mixture is heated to 180°C for six hours. The mixture is cooled, diluted with 200 ml. of chloroform, filtered, and evaporated to yield methyl 1-methyl-6-methoxy-2-naphthylacetate.

Workup

  1. additionTo a mixture of 12 g
  2. temperatureThe alkylating mixture is refluxed for one hour after it
  3. additionthe mixture is made acidic to litmus by the addition of 1N methanolic HC1
  4. filtrationfiltered
  5. customevaporated
  6. additionThe residue, containing methyl 1-methyl-6-methoxy-3,4-dihydro-2-naphthylacetate
  7. additionis added to 1 g
  8. temperatureThe mixture is cooled
  9. additiondiluted with 200 ml
  10. filtrationof chloroform, filtered
  11. customevaporated

Sources & evidence

ORD record
ord-a2b37f9be1da416b95b34f2642c7997b
Source dataset
uspto-grants-1976_08
Patent number
US03978116

Reaction notes

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