Carbon Disulfide → 2-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 398303

Reaction equation

HRID 398303 reaction equation
[CH2:1]([C:7]1[CH:12]=C[CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:18]([CH3:26])([CH2:20][CH2:21][C:22](Cl)([CH3:24])[CH3:23])[CH3:19].[C:27](=S)=S>>[CH3:19][C:18]1([CH3:26])[C:10]2[C:23](=[CH:12][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=2)[C:22]([CH3:27])([CH3:24])[CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 6348Carbon DisulfideHCID 14109HexylbenzeneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 230025302-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

Conditions

Temperature
0 °C

Procedure

83 ml of hexylbenzene were treated with 1.8 g of aluminium chloride while cooling with ice. After brief stirring a solution of 40 g of 2,5-dichloro-2,5-dimethyl-hexane in 300 ml of carbon disulphide was added dropwise and the mixture was stirred at 0° C. for a further 2 hours. The reaction mixture was poured into ice/6N hydrochloric acid, extracted with ethyl acetate, dried over sodium sulphate and evaporated. The crude product was distilled in a high vacuum. There were obtained 25.5 g of 1,1,4,4-tetramethyl-6-hexyl-1,2,3,4-tetrahydro-naphthalene as a colourless oil, boiling point 141-152° C./0.8 mm.

Workup

  1. temperaturewhile cooling with ice
  2. additionwas added dropwise
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. distillationThe crude product was distilled in a high vacuum

Sources & evidence

ORD record
ord-39072a6ec0c646aa996354032aa94953
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Linked notes

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