Hydrochloric Acid → HCID 53705215, compound

HRID 840020Notes

Reaction equation

HRID 840020 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.Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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-(methoxycarbonyl-methylene)-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 HCl, 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 6 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. filtrationfiltered
  4. customevaporated
  5. additionThe residue, containing methyl 1-methyl-6-methoxy-3,4-dihydro-2-naphthylacetate
  6. additionis added to 1 g
  7. temperatureThe mixture is cooled
  8. additiondiluted with 200 ml
  9. filtrationof chloroform, filtered
  10. customevaporated

Sources & evidence

ORD record
ord-68ea410435c54915aee8de3fd346b268
Source dataset
uspto-grants-1978_06
Patent number
US04097674

Reaction notes

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