4-Hydroxybenzaldehyde → 4-Isopropoxybenzaldehyde

HRID 1594950Notes

Reaction equation

HRID 1594950 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 63582-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 2500774-IsopropoxybenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-hydoxybenzaldehyde (4.0 g, 32.8 mmol) in dry DMF (100 mL) was added 2-bromopropane (6.0 g, 49.2 mmol) and potassium carbonate (6.8 g, 49.2 mmol). The resulting reaction was heated to 100° C. and stirred for 3 hours. The reaction was quenched by adding excess water and partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum. Purification on silica gel with 15% ether/hexane afforded the title compound (5.0 g, 93%).

Workup

  1. customThe resulting reaction
  2. customThe reaction was quenched
  3. additionby adding excess water
  4. custompartitioned between ethyl acetate and brine
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customPurification on silica gel with 15% ether/hexane

Sources & evidence

ORD record
ord-57ded30193674e18993c1d68b62f854a
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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