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

HRID 484355Notes

Reaction equation

HRID 484355 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>[CH3:5][C:6]1([CH3:18])[CH2:7][CH2:8][C:9]([CH3:17])([CH3:16])[C:10]2[CH:11]=[C:12]([C:19](=[O:21])[CH3:20])[CH:13]=[CH:14][C:15]1=2

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 with stirring with a mixture of 4 g (21.2 mmol) 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene and 1.94 g (24.7 mmol) acetyl chloride via a dropping funnel over a period of thirty minutes. The cooling bath was removed and the mixture stirred for 2 hours, then quenched with ice. The organic layer was separated and the aqueous layer extracted with 2×50 ml methylene chloride. Organic extracts were combined and washed with water and saturated NaHCO3 solution and then dried (MgSO4). Solvent was removed in-vacuo and the residue distilled by the kugelrohr method (90° C.; 0.45 mm) to give the title compound as a colorless oil. PMR (CDCl3): δ 1.32 (6H, s), 1.33 (6H, s), 1.72 (4H, s), 2.60 (3H, s), 7.41 (1H, d, J~8.9 Hz), 7.71 (1H, dd, J~8.8, 2.6 Hz) 7.96 (1H, d, J~2.6 Hz).

Workup

  1. temperaturewas cooled under argon in an ice-salt bath
  2. additiontreated
  3. customThe cooling bath was removed
  4. customquenched with ice
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted with 2×50 ml methylene chloride
  7. washwashed with water and saturated NaHCO3 solution
  8. dry with materialdried (MgSO4)
  9. customSolvent was removed in-vacuo
  10. distillationthe residue distilled by the kugelrohr method (90° C.; 0.45 mm)

Sources & evidence

ORD record
ord-9f870cf85e0642949767950fe138d6fb
Source dataset
uspto-grants-1993_07
Patent number
US05231113

Reaction notes

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