6-Bromohexanoyl chloride → 6-Bromo-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-1-hexanone

HRID 2108264Notes

Reaction equation

HRID 2108264 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[C:5]([CH3:11])[C:4]=1[O:12][CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([C:7]1[C:6]([CH3:10])=[C:5]([CH3:11])[C:4]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[C:8]=1[CH3:9])=[O:25]

Participants

5

Reactant 3

HCID 898486-Bromohexanoyl chloride2×HCID 6451240Aluminum(III) Chloride2×HCID 14986428Dimethoxy-3,4,6-trimethylbenzene

Product 1

HCID 149864296-Bromo-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-1-hexanoneYield 16.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.956 g (16 mmol) of 1,2-dimethoxy-3,4,6trimethylbenzene in 10 mL of methylene chloride was added to 2.40 g (18 mmol) of aluminum chloride and 3.80 g (18 mmol) of 6-bromohexanoyl chloride in 30 mL of methylene chloride cooled in an ice bath. The solution was kept at 3° for 45 minutes and then at 23° for 42 hours. An additional 2.0 g of aluminum chloride and 3.0 g of 6-bromohexanoyl chloride were added and the reaction mixture was stirred at reflux for 22 hours. Workup as in Example 16 and purification by HPLC using 4% ethyl acetate-hexane gave 0.95 g of 6-bromo-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-1-hexanone as an oil. The nmr spectrum was consistent with the structure and the mass spectrum gave a molecular ion at m/z 356 (C17H25BrO3).

Workup

  1. temperaturecooled in an ice bath
  2. waitat 23° for 42 hours
  3. temperatureat reflux for 22 hours
  4. customWorkup as in Example 16 and purification by HPLC

Sources & evidence

ORD record
ord-11cb897d8a8d45c9ba459a73c6ca0ab4
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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