Hydrochloric Acid → Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-

HRID 2259991Notes

Reaction equation

HRID 2259991 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].C[C:10]1[CH:11]=[CH:12][C:13]2[C:14]([CH3:23])([CH3:22])[CH2:15][CH2:16][C:17]([CH3:21])([CH3:20])[C:18]=2[CH:19]=1.Cl.[CH2:25](Cl)Cl>>[CH3:10][C:11]1[C:6]([C:5]([CH3:25])=[O:7])=[CH:19][C:18]2[C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15][C:14]([CH3:23])([CH3:22])[C:13]=2[CH:12]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 6367Acetyl chlorideHCID 811871,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthaleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 87186Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-

Procedure

To a suspension of 6.71 g (50.3 mmol) of aluminum chloride in methylene chloride at 0° C. under argon was added a solution of 3.95 g (3.58 mL, 50.3 mmol) of acetyl chloride and 10.21 g (41.9 mmol) of 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalene in methylene chloride. The resulting mixture was allowed to warm to room temperature over a period of 3 hours with stirring. The mixture was recooled to 0° C. and 1N HCl was dropwise added. The mixture was then taken-up in water and extracted three times with methylene chloride. The organic layers were washed with 1N HCl, water, brine, and dried (MgSO4). Solvent was removed in-vacuo and the resulting residue purified using flash chromatography to give the title compound as an ivory solid.

Workup

  1. customwas recooled to 0° C.
  2. extractiontaken-up in water and extracted three times with methylene chloride
  3. washThe organic layers were washed with 1N HCl, water, brine
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in-vacuo
  6. customthe resulting residue purified

Sources & evidence

ORD record
ord-50ff0cd1113b4ed795f636d0807702da
Source dataset
uspto-grants-1995_12
Patent number
US05475113

Reaction notes

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