3-Hydroxybenzaldehyde → 3-Propoxybenzaldehyde

HRID 587001

Reaction equation

HRID 587001 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH3:19].O>CN(C=O)C>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 27604693-PropoxybenzaldehydeYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (10.0 g) in DMF (120 ml) were added potassium carbonate (15.8 g) and 1-bromopropane (12.1 g), and the mixture was stirred under nitrogen atmosphere at room temperature overnight. Then, water was added to the mixture, which was extracted with ethyl acetate and washed with 1N sodium hydroxide solution twice, with water three times and with saturated brine once. After dried with magnesium sulfate, the solvent was evaporated under reduced pressure to give 3-propoxybenzaldehyde (13.4 g) as colorless liquid.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washwashed with 1N sodium hydroxide solution twice
  3. dry with materialAfter dried with magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e532573e9813427585e1ab5d71970579
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Linked notes

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