Water → 6-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

HRID 840471

Reaction equation

HRID 840471 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].Cl[C:6]([CH3:14])([CH2:8][CH2:9][C:10](Cl)([CH3:12])[CH3:11])[CH3:7].O.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]>>[Br:16][C:17]1[C:18]([CH3:23])=[CH:19][C:20]2[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][C:6]([CH3:14])([CH3:7])[C:21]=2[CH:22]=1

Participants

5

Reactant 4

HCID 962WaterHCID 72362-Bromotoluene2×HCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 100393466-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

Procedure

30 ml of 2-bromotoluene and 14 g (0.11 mol) of AlCl3 were introduced into a three-necked flask, cooling was carried out to 0° C. and a solution of 50 g (0.27 mol) of 2,5-dichloro-2,5-dimethylhexane in 100 ml of 2-bromotoluene was added dropwise, and the reaction mixture was permitted to heat to room temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic phase was separated by settling, washed with an aqueous sodium bicarbonate solution and evaporated. The product crystallized on stirring in methanol. After filtration, 56.9 g (75%) of 2-bromo-5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalene, with a melting-point of 92°-93° C., were recovered.

Workup

  1. temperaturecooling
  2. customwas carried out to 0° C.
  3. extractionextracted with dichloromethane
  4. customThe organic phase was separated
  5. washwashed with an aqueous sodium bicarbonate solution
  6. customevaporated
  7. customThe product crystallized
  8. filtrationAfter filtration, 56.9 g (75%) of 2-bromo-5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalene
  9. customa melting-point of 92°-93° C.
  10. customwere recovered

Sources & evidence

ORD record
ord-74fea49a9f0c4ff39a1a9519cc837b0f
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Linked notes

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