Hydrochloric Acid → (S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthalene

HRID 35751

Reaction equation

HRID 35751 reaction equation
[H-].[Li+].[H-].[Li+].[Al+3].[H-].[H-].[H-].Cl[CH2:10][C@@H:11]1[C:20]([CH3:22])([CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]([CH3:25])([CH3:24])[CH2:12]1.Cl>O1CCCC1>[CH3:24][C:13]1([CH3:25])[C:14]2[C:19](=[CH:18][C:17]([CH3:23])=[CH:16][CH:15]=2)[C:20]([CH3:22])([CH3:21])[C@@H:11]([CH3:10])[CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62714Lithium hydrideHCID 13175029(S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 21226445Aluminium lithium hydride

Product 1

HCID 13175223(S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthaleneYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium hydride (4.52 g; 0.569 mol) and aluminum lithium hydride (1.81 g; 0.048 mol) in tetrahydrofuran under nitrogen, (S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (94.69 g; 0.378 mol) was added dropwise, and the resultant mixture was heated while refluxing for 36 hours. The reaction mixture was treated with dilute hydrochloric acid and extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried, concentrated and distilled to give (S)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (59.7 g; 0.276 mol).

Workup

  1. temperaturewhile refluxing for 36 hours
  2. extractionextracted with n-hexane
  3. washThe extract was washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-c06f0207e593442db845f254e6ee523b
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Linked notes

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