Water → 4-isopropoxy-3-methoxybenzaldehyde

HRID 1944108Notes

Reaction equation

HRID 1944108 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH3:21])[CH3:20].O>CN(C=O)C>[CH:19]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 63582-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 7082534-isopropoxy-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-hydroxy-3-methoxybenzaldehyde (100 g), potassium carbonate (182 g) and 2-bromopropane (81 ml) in DMF (500 ml) was stirred at 65° C. for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad006e3382e3496ea281420c13429fbb
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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