Acetyl chloride → 1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

HRID 128916

Reaction equation

HRID 128916 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:17])([CH3:16])[CH2:8][CH2:7]1.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[CH3:16][C:9]1([CH3:17])[C:10]2[C:15](=[CH:14][C:13]([C:19](=[O:21])[CH3:20])=[CH:12][CH:11]=2)[C:6]([CH3:18])([CH3:5])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 811861,1,4,4-TetramethyltetralinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3.45 g (25.9 mmol) aluminum chloride in 15 ml methylene chloride was cooled under argon in an ice/salt bath and treated while stirring with a mixture of 4 g (21.2 mmol) 1,1,4,4-tetramethyl-1,2,3,4-tetrahydro naphthalene (from Example 2) and 1.94 g (24.7 mmol) acetylchloride via a dropping funnel over a period of 0.5 hours. Then the cooling bath was removed, the mixture stirred for 2 hours at room temperature and the reaction quenched with ice. The organic layer was recovered and the aqueous layer extracted with 2×50 ml methylene chloride.

Workup

  1. temperaturewas cooled under argon in an ice/salt bath
  2. additiontreated
  3. customThen the cooling bath was removed
  4. customthe reaction quenched with ice
  5. customThe organic layer was recovered
  6. extractionthe aqueous layer extracted with 2×50 ml methylene chloride

Sources & evidence

ORD record
ord-c6c22427f8e24fa889405737e7c72cfe
Source dataset
uspto-grants-1995_11
Patent number
US05466690

Linked notes

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