Hydrochloric Acid → 9-Methylphenanthrene

HRID 868765Notes

Reaction equation

HRID 868765 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li][CH2:17]CCC.COS(OC)(=O)=O.Cl>CCOCC>[CH3:17][C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 113099-BromophenanthreneHCID 178418339Butyllithium

Product 1

HCID 134389-Methylphenanthrene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

9-Bromophenanthrene (27 g, 102 mmol) was dissolved in 400 mL of dry ether and cooled to −78° C. 170 mL of BuLi (1.6 M in hexane) was slowly added into this solution in 45 minutes. The reaction mixture was warmed to room temperature. The mixture was then stirred at room temperature for 2 h before it was cooled to −78° C. again and Me2SO4 (17.6 g, 133 mmol) in ether was slowly added. The mixture was stirred at room temperature for 10 h. The mixture was poured into 15% HCl aqueous solution and extracted with CH2Cl2 and dried over MgSO4. The solvent was evaporated to give a residue which was recrystallized from hexane to yield 14.2 g of product as a white solid.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperaturewas cooled to −78° C. again
  3. stirringThe mixture was stirred at room temperature for 10 h
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. customto give a residue which
  8. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-3ea39e71de1e4b1ea9cc9f364e2a6bc8
Source dataset
uspto-grants-2015_03
Patent number
US08968887B2

Reaction notes

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