Water → HCID 14986401, compound

HRID 2108263Notes

Reaction equation

HRID 2108263 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][CH3:10])[C:3]=1[O:11][CH3:12].[Cl-].[Al+3].[Cl-].[Cl-].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24].O>C(Cl)Cl>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([C:7]1[CH:6]=[C:5]([CH3:8])[C:4]([O:9][CH3:10])=[C:3]([O:11][CH3:12])[C:2]=1[CH3:1])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 898486-Bromohexanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 13697581HCID 13697581, compound

Product 1

HCID 14986401HCID 14986401, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.227 g (1.5 mmol) of 3,6-dimethylveratrole in 1 mL of methylene chloride was added to an ice cooled mixture of 0.245 g (1.8 mmol) of aluminum chloride and 0.416 g (1.9 mmol) of 6-bromohexanoyl chloride in 3 mL of methylene chloride. The reaction mixture was kept at 0° for 19 hours. Water was added and the organic layer was separated and washed with sodium bicarbonate solution. The dried extract was concentrated to an oil which was chromatographed on 60 g of silica gel using 10% ethyl acetate-hexane to give 0.235 g of 6-bromo-1-(3,4-dimethoxy-2,5-dimethylphenyl)-1-hexanone as an oil. The nmr spectrum was consistent with the structure and the mass spectrum gave the molecular ion at m/z 342 (C16H23BrO3).

Workup

  1. temperaturecooled
  2. customthe organic layer was separated
  3. washwashed with sodium bicarbonate solution
  4. extractionThe dried extract
  5. concentrationwas concentrated to an oil which
  6. customwas chromatographed on 60 g of silica gel using 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-c614f30d245b45b8bfc5c30664faca38
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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