Hydrochloric Acid → 7-Acetyl-1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene

HRID 35758Notes

Reaction equation

HRID 35758 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5]([CH3:14])([CH3:13])[CH2:4][CH:3]1[CH3:15].[C:17](Cl)(=[O:19])[CH3:18].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)C>[C:17]([C:9]1[CH:10]=[C:11]2[C:6]([C:5]([CH3:14])([CH3:13])[CH2:4][CH:3]([CH3:15])[C:2]2([CH3:16])[CH3:1])=[CH:7][C:8]=1[CH3:12])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 143438971,1,2,4,4,6-Hexamethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 2276507-Acetyl-1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthaleneYield 77.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution 1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (21.0 g; 0.097 mol) and acetyl chloride (8.0 g; 0.102 mol) in dichloroethane (60 g), anhydrous aluminum chloride (14.9 g; 0.112 mol) was added, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was treated with dilute hydrochloric acid. The organic layer was separated, washed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution, dried and concentrated to give 7-acetyl-1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (19.3 g; 0.075 mol; 77%). B.P., 109° C./0.2 mmHg. M.P., 61.5°-62.5° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef44da8b4da047fa89ea6fa071ff24b1
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Reaction notes

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