Dimethylformamide → 3-Isopropoxybenzaldehyde

HRID 1594948Notes

Reaction equation

HRID 1594948 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:9]([CH3:11])[CH3:10])[CH:3]=1.[Li]CCCC.CN([CH:20]=[O:21])C>C1COCC1.CCCCCC>[CH:9]([O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:20]=[O:21])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 32608011-Bromo-3-isopropoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 7129143-IsopropoxybenzaldehydeYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-bromo-3-iso-propyloxybenzene (2.16 g, 10 mmol) in dry THF (30 mL) was cooled to −78° C. and n-BuLi (4.8 mL of a 2.5 m solution in hexane, 12 mmol) was added. The resulting solution was stirred 0.5 hours and DMF (7.3 g, 10 mmol) was added at −78° C. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated under vacuum. Purification on silica gel with 25% ethyl acetate/hexane afforded the title compound (1.64 g, 100%).

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification on silica gel with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-76949924215b4a11943f082d9bb2b7d7
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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