Aluminum(III) Chloride → 5-methoxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one

HRID 514034Notes

Reaction equation

HRID 514034 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH:14]([CH3:19])[CH2:15][C:16](Cl)=[O:17]>C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:8]=1[CH2:13][CH:14]([CH3:19])[CH2:15][C:16]2=[O:17]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 866915384-(2-Methoxyphenyl)-3-methylbutyryl chloride

Product 1

HCID 638208135-methoxy-3-methyl-3,4-dihydro-2H-naphthalen-1-oneYield 36.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of AlCl3 (6.4 g) and CH2Cl2 (100 mL) was cooled to 0° C. To the mixture was added 4-(2-methoxyphenyl)-3-methylbutyryl chloride (24 mmol, crude from previous reaction). The reaction was allowed to warm slowly to room temperature and then quenched by slowly pouring over ice. The mixture was extracted with dichloromethane (3×) and the combined organics were washed with 1 M HCl, water, dried over sodium sulfate, and concentrated. Purification by flash column chromatography yielded the desired product (1.65 g, 36% yield from 4-(2-methoxy-phenyl)-3-methyl-but-2-enoic acid ethyl ester). LCMS-ESr (m/z): [M+H]+ calcd for C12H15O2: 191.11. Found: 191.19.

Workup

  1. temperatureto warm slowly to room temperature
  2. customquenched
  3. additionby slowly pouring over ice
  4. extractionThe mixture was extracted with dichloromethane (3×)
  5. washthe combined organics were washed with 1 M HCl, water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-455b430f90d441f190ff26f57734d93b
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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