Hydrochloric Acid → HCID 131714152, compound

HRID 2164469Notes

Reaction equation

HRID 2164469 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Na:11].C1(P2C=C(C)C(C)=C2)C=CC=CC=1.[Mg+2:25].[Br-:26].[Br-].[S].Cl>C1COCC1>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1.[Na:11].[Mg+2:25].[Br-:26].[Br-:26]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 931NaphthaleneHCID 82241Magnesium BromideHCID 635827HCID 635827, compoundHCID 5360545Sodium2×HCID 5362487Sulfur

Product 1

HCID 131714152HCID 131714152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

In a well dried Erlenmeyer flask 6 g of naphthalene (0.047 mole) were dissolved in 100 cm3 of THF. 1 g of sodium (0.043 at-g) cut into small pieces was added. When all the sodium had reacted (about 1 hour), 4 cm3 of 1-phenyl-3,4-dimethyl phosphole (0.0213 mole) were added. The mixture was left to react for 5 hours at room temperature. Then 4 g of anhydrous MgBr2 (0.0218 mole) was added and it was left to react further for 1 hour. It was transferred under argon into a dropping funnel and was added, drop by drop, to a solution of 0.025 mole of X--(CH2)nZ in 50 cm3 of THF. It was subjected to stirring over night. The next day, 1 g of flowers of sulfur (0.03 at-g) was added, and it was heated for 2 hours on an oil bath at 70° C. It was allowed to cool down, hydrolysed, neutralized if necessary with dilute HCl, the THF driven off, the residue extracted with methylene chloride, dried over Na2SO4 and evaporated to dryness. The essential part of the naphthalene was removed by sublimation at 40° C. under 1 torr. The residue was chromatographed on silica gel passing a sieve with meshes of 0.210 to 0.062 mm.

Workup

  1. additionwas added
  2. additionwere added
  3. waitThe mixture was left
  4. customto react for 5 hours at room temperature
  5. waitit was left
  6. customto react further for 1 hour
  7. customIt was transferred under argon into a dropping funnel
  8. additionwas added
  9. temperatureto cool down
  10. extractionthe residue extracted with methylene chloride
  11. dry with materialdried over Na2SO4
  12. customevaporated to dryness
  13. customThe essential part of the naphthalene was removed by sublimation at 40° C. under 1 torr
  14. customThe residue was chromatographed on silica gel passing a sieve with meshes of 0.210 to 0.062 mm

Sources & evidence

ORD record
ord-ca99c39243a54c1cbb2c37ee79e9ed79
Source dataset
uspto-grants-1985_03
Patent number
US04504683

Reaction notes

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