# US 6,723,856 B1 · Process for the preparation of 2-acetyl-1-pyrroline, the basmati rice flavorant

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- Number: US 6,723,856 B1
- Document ID: US6723856B1
- Status: Granted
- Kind: B1
- Application number: 10/400,913
- Filed: 2003-03-28
- Granted: 2004-04-20
- Earliest claimed: 2003-03-28
- Assignees: Council of Scientific and Industrial Research
- Inventors: Pullabhatia Srinivas; Kambadoor Nagarajarao Gurudutt
- Web page: https://patentgrep.com/patent/US6723856B1

## CPC

- C07D 207/20: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A23L 27/2054: {having nitrogen as the only hetero atom}
- A23L 27/2056: {having at least two different hetero atoms, at least one being a nitrogen atom}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)

## Abstract

The present invention provides a process for preparing of 2-acetyl-1-pyrroline, the principle aroma component of basmati and other varieties of scented rice, and also of processed cereal and grain products, said flavor chemical is of great value, in the art of application of flavor to foodstuffs like rice and bakery products.

## Claims

### Claim 1

An improved process for the preparation of 2-acetyl-1-pyrroline, the said process comprising steps of:
a) dissolving L-proline in dry alcohol, cooling to a temperature in the range of −5° C. to −15° C.,
b) adding thionylchloride to step (a) solution, maintaining the temperature of reactant mixture below 0° C.,
c) stirring the reactant mixture of step (b) at a temperature range of 20° to 30° C. for a time period of 1 h to 4 h,
d) removing the solvent from reactant mixture of step (c) to obtain a residue, which is stored in ice-chest for a time period of 10 h to 16 h to obtain a solid mass,
e) adding the solid mass of step (d) to 50% aqueous alkali carbonate solution, extracting with an organic solvent, separating the organic and aqueous layer,
f) drying the organic layer of step (e) over anhydrous sodium sulphate, filtering, evaporating the solvent from filtrate to obtain a residue,
g) distilling the residue of step (f) to obtain 2-carbomethoxy-1-pyrrolidine,
h) dissolving 2-carbomethoxy-1-pyrrolidine of step (g) in ether, cooling to a temperature range of 0° to 5° C., adding drop wise t-butylhypochlorite over a period of 10 minutes to 30 minutes, stirring at a temperature range of 20° to 30° C. for a time period of 4 h to 6 h,
i) filtering the solution of step (h), removing the solvent from the filtrate to obtain 2-carbomethoxy-1-pyrroline,
j) preparing Grignard Reagent in dry ether by adding magnesium turning, iodine followed by dropwise methyl iodide and stirring at a temperature in the range of 25° C. to 35° C. for completion of reaction, cooling the mixture to 0° C.,
k) adding an ethereal solution of 2-carbomethyoxy-1-pyrroline to the cooled mixture of step (j), stirring at a room temperature till the reaction is complete,
k) adding 5% aqueous hydrochloric acid to step (k) mixture, extracting with diethyl ether, separating the organic layer, drying the organic layer over anhydrous sodium sulphate, filtering to obtain a filtrate, and
l) distilling the filtrate of step (i) to obtain pure 2-acetyl-1-pyrroline.

### Claim 2 (depends on 1)

The process of claim 1, wherein in step (a) the dry alcohol used, is selected from a group consisting of dry methanol, ethanol and propanol.

### Claim 3 (depends on 2)

The process of claim 2, wherein the dry alcohol used is dry methanol.

### Claim 4 (depends on 1)

The process of claim 1, wherein in step (e) the organic solvent used is selected from a group consisting of dimethyl ether, diethyl ether and di-isopropyl ether.

### Claim 5 (depends on 4)

The process of claim 4, wherein the solvent used is diethyl ether.

### Claim 6 (depends on 1)

The process of claim 1, wherein in step (e) the aqueous alkali carbonate solution used, is selected from a group consisting of 50% aqueous sodium carbonate and 50% aqueous potassium carbonate.

### Claim 7 (depends on 1)

The process of claim 1, wherein in step (h) the dehydrogenation can be performed using potassium acetate.

### Claim 8 (depends on 1)

The process of claim 1, wherein the 2-acetyl-1-pyrroline obtained has a basmati rice flavor or popcorn flavor.

### Claim 9 (depends on 1)

The process of claim 1, wherein the 2-acetyl-1-pyrroline obtained is used in flavoring agent in food products, bakery products, food drinks and rice products.