4-Hydroxybenzaldehyde → 4-(Cyclopropylmethoxy)benzaldehyde

HRID 1485056Notes

Reaction equation

HRID 1485056 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]1[CH2:20][CH2:19]1>CC(C)=O>[CH:18]1([CH2:17][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 5432414-(Cyclopropylmethoxy)benzaldehydeYield 91.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-hydroxybenzaldehyde (2.00 g), potassium carbonate (4.53 g) and acetone (50.0 mL), (bromomethyl)cyclopropane (3.32 g) was added and the mixture was refluxed for 9 hours. After cooling the reaction mixture to room temperature, the resulting precipitate was removed by filtration through Celite (registered trademark). The filtrate was concentrated under reduced pressure and, thereafter, the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-50:50) to give the titled compound as a colorless oil (2.63 g).

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 9 hours
  3. customthe resulting precipitate was removed by filtration through Celite (registered trademark)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-50:50)

Sources & evidence

ORD record
ord-7126be6f684c46649b6767ebd4077f8c
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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