Phosphorus pentachloride → Methyl 1-chloro-6-methoxy-2-naphthaleneacetate

HRID 1284343Notes

Reaction equation

HRID 1284343 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6]2.P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1C=CC=CC=1>[Cl:20][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 13934507Methyl 1,2,3,4-tetrahydro-6-methoxy-1-oxo-2-naphthaleneacetate

Product 1

HCID 54157069Methyl 1-chloro-6-methoxy-2-naphthaleneacetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 25 g. of 6-methoxy-2-(methoxycarbonylmethyl)-1-tetralone and 150 ml. of benzene, 21 g. of phosphorus pentachloride are slowly added. After the addition, the chlorination mixture is allowed to stand for an additional five hours; then it is added to 500 g. of ice and extracted with xylene. The extracts, containing methyl 1-chloro-6-methoxy-3,4-dihydro-2-naphthylacetate, are combined, washed with water to neutrality and dried over sodium sulfate; then 23 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone are added and the resulting mixture is refluxed for five hours. The dehydrogenation mixture is cooled, filtered, and evaporated. The residue is taken up in acetone and chromatographed on alumina and evaporated to yield methyl 1-chloro-6-methoxy-2-naphthylacetate.

Workup

  1. additionTo a mixture of 25 g
  2. additionAfter the addition
  3. additionthen it is added to 500 g
  4. extractionof ice and extracted with xylene
  5. additionThe extracts, containing methyl 1-chloro-6-methoxy-3,4-dihydro-2-naphthylacetate
  6. washwashed with water to neutrality
  7. dry with materialdried over sodium sulfate
  8. additionof 2,3-dichloro-5,6-dicyano-1,4-benzoquinone are added
  9. temperaturethe resulting mixture is refluxed for five hours
  10. temperatureThe dehydrogenation mixture is cooled
  11. filtrationfiltered
  12. customevaporated
  13. customchromatographed on alumina
  14. customevaporated

Sources & evidence

ORD record
ord-a92dab58508041669a02b8c1ffc37f49
Source dataset
uspto-grants-1976_08
Patent number
US03978116

Reaction notes

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