Hydrochloric Acid → 1,1,2,4,4,6-Hexamethyl-1,2,3,4-tetrahydronaphthalene

HRID 35753Notes

Reaction equation

HRID 35753 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl[CH2:8][CH:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:21])[CH:15]=2)[C:10]1([CH3:23])[CH3:22].Cl>O1CCCC1>[CH3:22][C:10]1([CH3:23])[C:11]2[C:16](=[CH:15][C:14]([CH3:21])=[CH:13][CH:12]=2)[C:17]([CH3:20])([CH3:19])[CH2:18][CH:9]1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 143438962-Chloromethyl-1,1,4,4,6-pentamethyl1,2,3,4-tetrahydronaphthaleneHCID 21226445Aluminium lithium hydride

Product 1

HCID 143438971,1,2,4,4,6-Hexamethyl-1,2,3,4-tetrahydronaphthaleneYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium aluminum hydride (6.5 g; 0.171 mol) in tetrahydrofuran in a nitrogen atmosphere, a solution of 2-chloromethyl-1,1,4,4,6-pentamethyl1,2,3,4-tetrahydronaphthalene (40.9 g; 0.163 mol) in tetrahydrofuran was added dropwise, and the resultant mixture was stirred at 70° C. for 15 hours. The reaction mixture was treated with aqueous tetrahydrofuran, dilute hydrochloric acid was added thereto, and the resultant mixture was extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give 1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (31.6 g; 0.144 mol; 88%). B.P., 78° C./1.2 mmHg. M.P., 35°-36° C.

Workup

  1. additionwas added
  2. extractionthe resultant mixture was extracted with n-hexane
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd68d3ee2bd849b0b772eae7767f27fa
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Reaction notes

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