Water → 6-Bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanone

HRID 2108262Notes

Reaction equation

HRID 2108262 reaction equation
[CH3:1][CH:2]([C:4]1[C:5]([O:12][CH3:13])=[C:6]([O:10][CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].O>C(Cl)Cl>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([C:8]1[CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[C:5]([O:12][CH3:13])=[C:6]([O:10][CH3:11])[CH:7]=1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 898486-Bromohexanoyl chlorideHCID 51528881-Isopropyl-2,3-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 149864006-Bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanoneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.0 g (0.028 mol) of 3-(1-methylethyl)-1,2-dimethoxybenzene in 5 mL of methylene chloride was added to an ice cooled mixture of 4.4 g (0.033 mol) of aluminum chloride and 7.0 g (0.033 mol) of 6-bromohexanoyl chloride in 50 mL of methylene chloride. The reaction mixture was kept at 0° for 18 hours. Water was added and the organic layer was separated and washed with sodium bicarbonate solution. The dried extract was concentrated under reduced pressure to an oil which was purified by HPLC using 5% ethyl acetate-hexane to give 8.1 g (82% yield) of 6-bromo-1-[3,4-dimethoxy-5-(1-methylethyl)-phenyl]-1-hexanone as an oil. The nmr spectrum was consistent with the structure and the mass spectrum gave the molecular ion at m/z 356 (C17H25BrO3).

Workup

  1. temperaturecooled
  2. customthe organic layer was separated
  3. washwashed with sodium bicarbonate solution
  4. extractionThe dried extract
  5. concentrationwas concentrated under reduced pressure to an oil which
  6. customwas purified by HPLC

Sources & evidence

ORD record
ord-f02fe7fc9acb4b4281357e752fd7890f
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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