Hydrochloric Acid → 6-Fluoro-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

HRID 1836882Notes

Reaction equation

HRID 1836882 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].Cl[C:10]([CH3:18])([CH2:12][CH2:13][C:14](Cl)([CH3:16])[CH3:15])[CH3:11].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[F:1][C:2]1[C:3]([CH3:8])=[CH:4][C:5]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][C:10]([CH3:18])([CH3:11])[C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72412-FluorotolueneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 234989346-Fluoro-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthaleneYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15 g (136 mmol) of 2-fluorotoluene and 24.9 g (136 mmol) of 2,5-dichloro-2,5-dimethylhexane in 120 mL dichloromethane was added 1.82 g (13.6 mmol) of aluminum chloride and the solution heated at reflux. After 18 hours the reaction mixture was cooled to room temperature and 5% aqueous HCl was added. This was partitioned between hexane and water. The aqueous phase was washed once with hexane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford 25.8 g (86%) of 2-fluoro-3-methyl-5 ,5 ,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (m.p.=90.0-91.8° C.).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux
  3. customThis was partitioned between hexane and water
  4. washThe aqueous phase was washed once with hexane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdde38ac824244c1b3d26943926c80e5
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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