Ethanol → HCID 12515243, compound

HRID 1111544Notes

Reaction equation

HRID 1111544 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].BrC.[CH2:20](O)[CH3:21]>>[CH2:20]([S:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1)[CH3:21]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 6323Methyl BromideHCID 70582-NaphthalenethiolHCID 11430Potassium Carbonate

Product 1

HCID 12515243HCID 12515243, compound

Procedure

To a solution, stirred under an inert atmosphere at ambient temperature, of 40 g of 2-mercapto naphthalene in 1 liter of anhydrous ethanol, there are slowly added 24.4 g of potash. The addition being completed, stirring is maintained for 2 hours, then there is slowly added a solution of 21 cm3 of bromomethane dissolved in 100 cm3 of anhydrous ethanol. After 3 hours of stirring, the reaction mixture is left overnight, then filtered and the filtrate is concentrated under a vacuum. The resulting crude product is stirred in 800 cm3 of water, then extracted 4 times with 150 cm3 of dichloromethane. The dichloromethane phases are combined, washed with a saturated solution of ammonium chloride, then dried on magnesium sulfate. The solvent is rectified under vacuum and 38 g of 2-ethylthio naphthalene are obtained and used as such for the following reactions.

Workup

  1. additionThe addition
  2. temperatureis maintained for 2 hours
  3. stirringAfter 3 hours of stirring
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under a vacuum
  6. stirringThe resulting crude product is stirred in 800 cm3 of water
  7. extractionextracted 4 times with 150 cm3 of dichloromethane
  8. washwashed with a saturated solution of ammonium chloride
  9. customdried on magnesium sulfate
  10. customare obtained

Sources & evidence

ORD record
ord-7ce2b6dffaab4979b3220471c6f320e1
Source dataset
uspto-grants-1990_12
Patent number
US04980509

Reaction notes

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