4-Hydroxybenzaldehyde → 2-(2-Propynyloxy)benzenecarbaldehyde

HRID 721965Notes

Reaction equation

HRID 721965 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]#C>C1(C)C=CC=CC=1.CC(C)=O>[CH2:10]([O:13][C:8]1[CH:9]=[CH:2][CH:3]=[CH:4][C:5]=1[CH:6]=[O:7])[C:16]#[CH:17]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 5830372-(2-Propynyloxy)benzenecarbaldehyde

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-hydroxybenzaldehyde (1 g, 8.2 mmol), of potassium carbonate (2.27 g, 16.4 mmol) and of propargyl bromide (1.4 ml of a solution at 80% in toluene) in 50 ml of anhydrous acetone is heated under reflux for 5 hours. The reaction medium is cooled to room temperature, filtered and concentrated. The crude reaction product obtained is purified using a chromatography column on silica gel, eluting with dichloromethane. 1.31 g (quantitative yield) of prop-2-ynyloxybenzaldehyde are obtained in the form of a white solid which is used as it is in the next step. 1H NMR (DMSO-d6, 400 MHZ, δ ppm): 9.89 (s, 1H); 7.89 (d, 2H); 7.18 (d, 2H); 4.95 (s, 2H); 3.65 (s, 1H).

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude reaction product
  5. customobtained
  6. customis purified
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6d4d7561d46749fd93e591dc701df895
Source dataset
uspto-grants-2006_11
Patent number
US07138108B2

Reaction notes

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