2-Bromopropane → 3-Isopropoxy-4-methoxybenzaldehyde

HRID 225513

Reaction equation

HRID 225513 reaction equation
[CH:1](Br)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[O:11]=[CH:12][C:13]1[CH:21]=[CH:20][C:17]([O:18][CH3:19])=[C:15]([OH:16])[CH:14]=1>CN(C=O)C.CCOCC>[CH:1]([O:16][C:15]1[CH:14]=[C:13]([CH:21]=[CH:20][C:17]=1[O:18][CH3:19])[CH:12]=[O:11])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 5920923-Isopropoxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Isopropyl bromide (19.0 mL, 200 mmol) was added to a suspension of K2CO3 (42.0 g, 302 mmol) and isovanillin (23 g, 151.3 mmol) in DMF (100 gmL) and the stirring slurry heated to 80° C. for 13 h. The reaction mixture was then cooled to room temperature, diluted with ether (200 mL) and washed with H2O (4×200 mL), dried (MgSO4) and concentrated under reduced pressure giving the title compound as a slightly tan oil (29.3 g, 100%) which required no further purification. The spectra of this material are identical with those previously reported (H. Ishii, I.-S. Chen and T. Ishikawa J. Chem. Soc., Perkin Trans. 1, 1987, 671.).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washwashed with H2O (4×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d8190cefb6c447897c48436ecc5f973
Source dataset
uspto-grants-2009_07
Patent number
US07557118B2

Linked notes

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