Process for preparing 2-acetonaphthones
AssigneeEastman Kodak Company
InventorJoseph R. Zoeller
Life of this patent
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Abstract
2-Acetonaphthones are prepared by heating a compound selected from the group consisting of ketals and enol ethers of acetyl-substituted benzalacetone at a temperature effective to cyclize the compound and form said 2-acetonaphthones.
Claims18
A process for preparing a 2-acetonaphthone of the formula ##STR5## wherein R.sup.1 is H, halo or (C.sub.1 -C.sub.12)alkoxy, acyloxy, carboxy, carbalkoxy, acyl, alkyl or thioalkyl, said process comprising heating at a temperature within the range of 150.degree. C. to 800.degree. C. and a pressure within the range of about 0.1 mmHg to 3 atm a compound selected from the group consisting of a ketal of the formula ##STR6## wherein R.sup.1 is described above, and each R.sup.2 is (C.sub.1 -C.sub.12)alkyl or the two R.sup.2 taken together are (C.sub.2 -C.sub.12)alkylene, or an enol ether of the formula ##STR7## wherein R.sup.1 is as defined above and R.sup.2 is (C.sub.1 -C.sub.12)alkyl or C.sub.2 -C.sub.12 acyl at a temperature effective to cyclize the compound and obtain said 2-acetonaphthones.
A process for preparing a 2-acetonaphthones of the formula ##STR8## wherein R.sup.1 is H, halo or (C.sub.1 -C.sub.12)alkoxy, acyloxy, carboxy, carbalkoxy, acyl, alkyl or thioalkyl, said process comprising reacting at a temperature in the range of -25.degree. to 250.degree. C. an acyl-substituted benzalacetone of the formula ##STR9## wherein R.sup.1 is as defined above, with a ketalizing agent selected from the group consisting of alkyl glycols and di-alkyl acetals, di-alkyl ketals, and tri-alkyl orthoesters;
- said benzalacetone and said ketalizing agent being present in a proportion and under conditions effective to form a compound selected from the group consisting of a ketal of an acetyl-substituted benzalacetone of the formula ##STR10## wherein R.sup.1 is as defined above, and R.sup.2 is (C.sub.1 -C.sub.12)alkyl or the two R.sup.2 taken together are (C.sub.1 -C.sub.12)alkylene, or an enol ether of an acetyl-substituted benzalacetone of the formula ##STR11## wherein R.sup.1 is as defined above and R.sup.2 is (C.sub.1 -C.sub.12)alkyl or (C.sub.2 -C.sub.12)acyl and heating said compound at a temperature effective to cyclize said compound and form said 2-acetonaphthone.
A process for producing a 2-acetonaphthone of the formula ##STR12## wherein R.sup.1 is H, halo or (C.sub.1 -C.sub.12)alkoxy, acyloxy, carboxy, carbalkoxy, acyl, alkyl or thioalkyl, and R.sup.1 is H, (C.sub.1 -C.sub.12)alkyl, (C.sub.6 -C.sub.20)aryl, (C.sub.7 -C.sub.21)alkaryl or araalkyl, said process comprising reacting at a temperature within the range of 350.degree. C. to 600.degree. C. and a pressure within the range of about 0.1 mmHg to atmospheric pressure acetylacetone with a benzaldehyde substituted with H, halo or, (C.sub.1 -C.sub.12)alkyl, carboxy, carbalkoxy, acyloxy, acyl, alkoxy or alkylthio;
- said diketone and said benzaldehyde being present in a proportion and under conditions effective to form an acyl-substituted benzalacetone of the formula ##STR13## wherein R.sup.1 is as defined above;
- reacting said benzalacetone with a ketalizing agent selected from the group consisting of alkyl glycols and di-alkyl acetals, di-alkyl ketals, and tri-alkyl orthoesters;
- said benzalacetone and said ketalizing agent being present in a proportion and under conditions effective to form a compound selected from the group consisting of a ketal of said benzalacetone of the formula ##STR14## wherein R.sup.1 is as defined above, and R.sup.2 is (C.sub.1 -C.sub.12)alkyl or the two R.sup.2 taken together are (C.sub.1 -C.sub.12)alkylene, or an enol ether of said benzalacetone of the formula ##STR15## wherein R.sup.1 is as defined above and R.sup.2 is (C.sub.1 -C.sub.12)alkyl or (C.sub.2 -C.sub.12)acyl, and heating said compound at a temperature effective to cyclize said compound and form said 2-acetonaphthone.
Dependencies are inferred from the claim text.