4-Hydroxybenzaldehyde → 4-Cyclopropoxybenzaldehyde

HRID 1485058Notes

Reaction equation

HRID 1485058 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+].CN(C)C=O.Br[CH:22]1[CH2:24][CH2:23]1>[I-].[K+].O>[CH:22]1([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 78037Bromocyclopropane

Product 1

HCID 714230394-Cyclopropoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To a mixture of 4-hydroxybenzaldehyde (1.20 g), potassium carbonate (2.04 g), potassium iodide (49.0 mg) and N,N-dimethylformamide (9.80 mL), bromocyclopropane (1.02 mL) was added and the mixture was stirred at 200° C. for 3 hours under irradiation with microwaves. After being cooled to room temperature, the reaction mixture was poured into water and extracted with diethyl ether three times. The combined organic layers were washed with saturated brine and thereafter passed through a phase separator to be concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-50:50) to give the titled compound as a colorless oil (510 mg).

Workup

  1. additionwas added
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with diethyl ether three times
  4. washThe combined organic layers were washed with saturated brine
  5. concentrationto be concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-50:50)

Sources & evidence

ORD record
ord-ce6e84bb1e504287b43128fca95f2c50
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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