Chloroacetyl chloride → 2-Chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethanone

HRID 1614396

Reaction equation

HRID 1614396 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[CH2:4][CH2:3]1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:19][CH2:20][C:21]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5]([CH3:13])([CH3:12])[CH2:4][CH2:3][C:2]2([CH3:14])[CH3:1])=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 811861,1,4,4-TetramethyltetralinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 147265332-Chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 68 g (0.36 mole) of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene in 200 ml of methylene chloride was added dropwise at 0°-5° C. to a solution of 72 g (0.55 mole) of anhydrous aluminum chloride and 40.7 g (0.36 mole) of chloroacetyl chloride in 270 ml of dry methylene chloride. Stirring was then carried out overnight at room temperature. The mixture was poured onto ice/water and extracted with methylene chloride, and the organic phase was washed several times with water, dried over sodium sulfate and evaporated down. 92.2 g of 6-chloroacetyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene remained as an oil. The structure was determined by H-NMR spectroscopy.

Workup

  1. additionThe mixture was poured onto ice/water
  2. extractionextracted with methylene chloride
  3. washthe organic phase was washed several times with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated down

Sources & evidence

ORD record
ord-87fb659916184dd7b49b3f486d29541e
Source dataset
uspto-grants-1993_03
Patent number
US05196532

Linked notes

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