4-Hydroxybenzaldehyde → 4-Isopropoxybenzaldehyde

HRID 1728258Notes

Reaction equation

HRID 1728258 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10](Br)([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:10]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 63582-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 2500774-IsopropoxybenzaldehydeYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
58 °C

Procedure

A solution of 30 g of 4-hydroxybenzaldehyde and 46 g of isopropyl bromide in 300 ml of N,N-dimethylformamide is treated with 104 g of finely powdered potassium carbonate and the mixture is stirred at 58° C. overnight. The suspension is suction filtered and the filtrate is concentrated in a vacuum. A solution of the residue in 100 ml of diethyl ether is washed twice with 100 ml of water each time, dried over sodium sulphate and concentrated. Chromatography of the crude product on silica gel with hexane/ethyl acetate (vol. 9:1) gives 40 g of 4-(isopropyloxy)benzaldehyde.

Workup

  1. filtrationsuction filtered
  2. concentrationthe filtrate is concentrated in a vacuum
  3. washA solution of the residue in 100 ml of diethyl ether is washed twice with 100 ml of water each time
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54e92f83a4de40ebaeb1ea4300134aa9
Source dataset
uspto-grants-1994_07
Patent number
US05326498

Reaction notes

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