Diethyl Ether → HCID 53970531, compound

HRID 2072557Notes

Reaction equation

HRID 2072557 reaction equation
[N+](=[CH2:3])=[N-].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12](O)[CH:11]([CH2:17][C:18]([OH:20])=[O:19])CC2.[CH2:21]([O:23][CH2:24][CH3:25])C>>[CH3:21][O:23][C:24]1[C:25]2[C:8](=[CH:7][C:6]([O:5][CH3:4])=[CH:15][CH:14]=2)[CH:13]=[CH:12][C:11]=1[CH2:17][C:18]([O:20][CH3:3])=[O:19]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 9550DiazomethaneHCID 21408130HCID 21408130, compound

Product 1

HCID 53970531HCID 53970531, compound

Conditions

Temperature
210 °C

Procedure

A solution of 4.2 g. of diazomethane and 75 ml. of diethyl ether is added to a mixture of 23.6 g. of 6-methoxy-1-hydroxyl-1,2,3,4-tetrahydro-2-naphthylacetic acid and 150 ml. of diethyl ether. The reaction mixture is stirred until colorless; then it is evaporated. The residue, containing methyl 6-methoxyl-1-hydroxy-1,2,3,4-tetrahydro-2-naphthylacetate is esterified by treatment with 240 mg. of sodium hydride in 25 ml. of methanol followed by the addition of 2.4 g. of methyl iodide. The product, methyl 1,6-dimethoxy-1,2,3,4,-tetrahydro-2-naphthylacetate, is dehydrogenated by heating it with 2 g. of 10% palladium-on-charcoal catalyst; the resulting mixture is heated to 210° C for 12 hours. The cooled mixture is then diluted with 150 ml. of methylene chloride, filtered, and evaporated to yield methyl 1,6-dimethoxy-2-naphthylacetate. The product is refluxed in a mixture of 150 ml. of glacial acetic acid and 150 ml. of 48% hydrobromic acid for 10 minutes. The product is extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered and evaporated to yield to a mixture of methyl 1-hydroxy-6-methoxy-2-naphthylacetate and methyl 1-methoxy-6-hydroxy-2-naphthylacetate. The compounds are separated by distillation under reduced pressure and identified by nuclear magnetic spectroscopy.

Workup

  1. customthen it is evaporated
  2. additionThe residue, containing methyl 6-methoxyl-1-hydroxy-1,2,3,4-tetrahydro-2-naphthylacetate
  3. additionof methanol followed by the addition of 2.4 g
  4. temperatureby heating it with 2 g
  5. additionThe cooled mixture is then diluted with 150 ml
  6. filtrationof methylene chloride, filtered
  7. customevaporated

Sources & evidence

ORD record
ord-7c9cc200330e475782ca776464a707eb
Source dataset
uspto-grants-1977_09
Patent number
US04051233

Reaction notes

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