Vanillin → 4-isopropoxy-3-methoxybenzaldehyde

HRID 225514Notes

Reaction equation

HRID 225514 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:18]([OH:19])=[C:15]([O:16][CH3:17])[CH:14]=1>CN(C=O)C.C(OCC)C>[CH:1]([O:19][C:18]1[CH:20]=[CH:21][C:13]([CH:12]=[O:11])=[CH:14][C:15]=1[O:16][CH3:17])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1183VanillinHCID 63582-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 7082534-isopropoxy-3-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Isopropyl bromide (40.0 mL, 421 mmol) was added to a suspension of K2CO3 (48.0 g, 348 mmol) and vanillin (40 g, 263 mmol) in DMF (150 mL) and the stirring slurry heated to 80° C. for 15 h. The reaction mixture was then cooled to room temperature, diluted with diethyl 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 (51.0 g, 100%) which required no further purification. The spectra of this material are identical with that previously reported (M. F. Comber and M. V. Sargent, J. Chem. Soc., Perkin Trans. 1, 1991, 2783).

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-ea40bce681c3461caeae8bee2349e0e2
Source dataset
uspto-grants-2009_07
Patent number
US07557118B2

Reaction notes

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