Acetyl chloride → 1-(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthyl)ethan-1-one

HRID 1883264Notes

Reaction equation

HRID 1883264 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]2([CH3:24])[CH3:23]>C(Cl)Cl>[CH3:9][O:10][C:11]1[C:20]([C:5](=[O:7])[CH3:6])=[CH:19][C:18]2[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 103310036-Methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene2×

Product 1

HCID 30179161-(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthyl)ethan-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of AlCl3 (6.6 g, 49.6 mmol) in CH2Cl2 (225 mL) at 0° C. was added acetyl chloride (3.5 mL, 49.6 mmol) dropwise via syringe. To the resulting homogeneous light brown solution was added 6-methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene (Intermediate 2, 9.0 g, 41.3 mmol) in CH2Cl2 (25 mL) via cannula. The mixture was then stirred at ambient temperature for 1 h, poured onto ice and extracted with Et2O (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give the title compound as a white solid (10.7 g, 100%).

Workup

  1. additionpoured onto ice
  2. extractionextracted with Et2O (×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-857aae56af414779a0c25da239c2db9e
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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