1,4-Dimethoxybenzene → HCID 14839562, compound

HRID 467163Notes

Reaction equation

HRID 467163 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.Cl[C:12]([CH3:20])([CH2:14][CH2:15][C:16](Cl)([CH3:18])[CH3:17])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:1][O:2][C:3]1[C:8]2[C:16]([CH3:18])([CH3:17])[CH2:15][CH2:14][C:12]([CH3:20])([CH3:13])[C:7]=2[C:6]([O:9][CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 90161,4-DimethoxybenzeneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 14839562HCID 14839562, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution, stirred at 0° C. under an inert atmosphere, of 165.5 g of 1,4-dimethoxybenzene and 218.7 g of 2,5dichloro-2,5 -dimethyl hexane, obtained in Example I(a), in 750 cm3 of anhydrous 1,2-dichloroethane, there are added, all at once, 31.9 g of powdered anhydrous aluminum chloride. The mixture is stirred for 1 hour at ambient temperature and then left to stand overnight. The next day after 4 hours stirring at this temperature, 600 cm3 of ice water are added. The organic phase is decanted and the aqueous phase is extracted three time with 400 cm3 of methylene chloride. The organic phases are combined, washed with water until neutral pH of the wash waters, then dried on sodium sulfate and concentrated. The resulting crude product is treated with animal charcoal in boiling ethanol, then recrystallized in this solvent. 195 g of 1,4-dimethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalene are obtained in the form of white needles having a melting point of 195° C.

Workup

  1. additionthere are added
  2. waitleft
  3. waitto stand overnight
  4. additionare added
  5. customThe organic phase is decanted
  6. extractionthe aqueous phase is extracted three time with 400 cm3 of methylene chloride
  7. washwashed with water until neutral pH of the wash waters
  8. customdried on sodium sulfate
  9. concentrationconcentrated
  10. additionThe resulting crude product is treated with animal charcoal
  11. customrecrystallized in this solvent

Sources & evidence

ORD record
ord-e02ef1a8d86b4efba12176cbc10075f0
Source dataset
uspto-grants-1992_10
Patent number
US05158977

Reaction notes

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