Hydrochloric Acid → 4'-Methyl[1,1'-biphenyl]-2-carbaldehyde

HRID 1977385Notes

Reaction equation

HRID 1977385 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.C[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1C=NC1CCCCC1.Cl.[CH2:27]1COCC1>>[CH3:27][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH:12]=[O:11])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 78054-BromotolueneHCID 8028Tetrahydrofuran3×HCID 5462224MagnesiumHCID 10775151123334-93-0

Product 1

HCID 13940094'-Methyl[1,1'-biphenyl]-2-carbaldehydeYield 51%

Procedure

To a suspension of magnesium metal (1.1 g) in THF (3 ml) was added dropwise a solution of 4-bromotoluene (7.5 g) in THF (10 ml) under gentle reflux. The resulting solution of the Grignard reagent was added dropwise to an ice-cooled, stirred solution of N-(2-methoxyphenyl)methylidenecyclohexylamine (4.3 g) in THF (30 ml). The reaction mixture was stirred at room temperature for 1.5 hours, followed by heating under reflux for 7 hours. After addition of ice-water, the reaction mixture was acidified with conc. hydrochloric acid. The reaction mixture was extracted with ethyl acetate and the extract was washed with 1N-hydrochloric acid and water, dried and evaporated to dryness. The residue was purified by column chromatography on silica gel to give pale yellow syrup (2.0 g, 51%).

Workup

  1. temperaturecooled
  2. temperatureby heating
  3. temperatureunder reflux for 7 hours
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe extract was washed with 1N-hydrochloric acid and water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9dd5e392a07c4292819c74a44d2b249c
Source dataset
uspto-grants-2001_05
Patent number
US06232334B1

Reaction notes

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