Diethyl Ether → HCID 53970531, compound

HRID 840019Notes

Reaction equation

HRID 840019 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-hydroxy-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-methoxy-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 ten 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 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-methoxy-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-02974d2dc938426981e08ca8558e2755
Source dataset
uspto-grants-1978_06
Patent number
US04097674

Reaction notes

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