* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With 1-(2-hydroxycarbonyl)ethyl-3-methyl-3H-imidazolium chloride at 100℃; for 12h; Sealed tube;
1-18 Examples 1-5
Add formic acid (2.2mmol),Geraniol (2.0mmol) and different ionic liquids (0.2mmol) were added to a 15mL glass reaction tube and sealed;Move to an oil bath set at 100°C, stir and heat for 12 hours;After the reaction is terminated, cool to room temperature;Then, 2 mL of cyclohexane was added to the reaction solution for extraction;Take the upper organic phase and concentrate to obtain geranyl formate;After the lower ionic liquid is dried in a vacuum drying oven at 120°C for 12 hours,It can be used directly for the next time.
81%
Stage #1: formic acid With acetic anhydride at 60℃; for 1h; Inert atmosphere;
Stage #2: Geraniol With sodium hydrogencarbonate at 20℃; for 3.5h; Inert atmosphere;
Rk. mit Monoperoxyphthalsaeure bei 0grad: rel. Geschwindigkeit;
Allyl-nicht-Allyl-Kopplung m. Organo-Al-Verbb.;
9
[ 98-01-1 ]
[ 105-86-2 ]
[ 5392-40-5 ]
Yield
Reaction Conditions
Operation in experiment
86%
With aluminum isopropoxide
2 Preparation of Citral from Furfural by Using Geranyl Formate
EXAMPLE 2 Preparation of Citral from Furfural by Using Geranyl Formate According to the same procedure of Example 1, using 19.5 g (200 mmol) of furfural, and 642 mg (3 mmol) of aluminum isopropoxide, 18.2 g (100 mmol) of geranyl formate was oxidized to obtain citral at a yield of 86%.
With hydrogenchloride; aluminum isopropoxide In water; toluene
1 Preparation of Citral from Geranyl Formate by Using Trimethylacetaldehyde
EXAMPLE 1 Preparation of Citral from Geranyl Formate by Using Trimethylacetaldehyde A dried 100 ml flask was charged and mixed with 18.2 g (100 mmol) of geranyl formate, 17.3 g (200 mmol) of trimethylacetaldehyde, and 642 mg (3 mmol) of aluminum isopropoxide in an atmosphere of nitrogen, followed by agitation at 40° C. for 3 hours. To the reaction mixture was added 20 ml of 1N hydrochloric acid and 30 ml of toluene, and phase-separated. The resultant organic phase was washed twice with 20 ml of 1N hydrochloric acid respectively, and further washed with 20 ml of water and separated, and washed with 5% sodium carbonate aqueous solution, thereafter distilled off the organic solvent under a reduced pressure, followed by distillation (at a boiling point of 68° C. at 0.3 mmHg) to obtain 13.68 g of citral (at a yield of 90%).
With sodium hydrogencarbonate In neat (no solvent) at 60℃; for 16h;
11 General procedure A: O-formylation of alcohols
General procedure: Alcohol (1.0 mmol) was added to (formyloxy)(phenyl)methyl acetate 1 (0.291 g, 1.5 mmol) and NaHCO3 (0.168 g, 2.0 mmol), and the reaction stirred at 60°C for 16 h. EtOAc (2 mL) was added as a cosolvent when the alcohol substrate was insoluble in the fomylating reagent at 60°C. The crude reaction mixture was then purified by column chromatography to give the desired formate ester.
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