Method of producing compounds containing acyloxyalkoxy groups from alcohols
AssigneeDixie Chemical Company
InventorJoseph C. Rongione
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Abstract
A process of producing compounds containing an acyloxyalkoxy group from an alcohol consists of reacting the alcohol with a formaldehyde donor until a compound of the formula: R--O--CH.sub.2 (OCH.sub.2).sub.X OR (V) is generated, wherein x is between about 1 to about 5 and R is an organic moiety. This product is then reacted with a carboxylic acid anhydride. The resulting product has the formula: R--O--CH.sub.2 O--COR.sup.1 wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group. The invention further relates to intermediates used in the production of such acyloxyalkoxylated compounds.
Claims24
A process of preparing a compound of the formula
- R--O--CH.sub.2 O--COR.sup.1 (I)
- wherein R is a C.sub.1 -C.sub.6 alkyl, a C.sub.3 -C.sub.8 cycloalkyl, an aryl or a benzyl group, the R group being optionally substituted with one or more phenoxy groups, benzyloxy groups, halogen atoms, a group of the formula:
- ##STR28## and --R.sup.8 --O--R.sup.9 ;
- wherein R.sup.7 and R.sup.9 independently are a C.sub.1 -C.sub.6 alkyl or haloalkyl group;
- R.sup.8 is of the formula --(CH.sub.2).sub.y wherein y is 0 to about 6;
- and R.sup.1 is a C.sub.1 -C.sub.6 alkyl, R.sup.1 being an organic moiety from a carboxylic acid anhydride, said process comprising reacting a polyoxymethylene of the formula:
- R--O--CH.sub.2 (OCH.sub.2).sub.x OR (V)
- wherein x is between 1 and 5 with a carboxylic acid anhydride containing about 2 to about 8 carbon atoms for a time and at a temperature sufficient to generate the compound of formula (I).
The process of preparing a compound of the formula:
- R--O--CH.sub.2 O--COR.sup.1 (I)
- wherein R is a C.sub.1 -C.sub.6 alkyl, a C.sub.3 -C.sub.8 cycloalkyl, an aryl or a benzyl group, the R group being optionally substituted with one or more phenoxy groups, benzyloxy groups, halogen atoms, a group of the formula:
- ##STR31## and --R.sup.8 --O--R.sup.9 wherein R.sup.7 and R.sup.9 independently are a C.sub.1 -C.sub.6 alkyl or haloalkyl group;
- R.sup.8 is a --(CH.sub.2).sub.y group wherein y is between 0 to about 6;
- and R.sup.1 is a C.sub.1 -C.sub.6 alkyl group;
- said process comprising:
- (a) reacting an alcohol of the formula R--OH and a formaldehyde donor in the presence of a catalyst for a time and at a temperature sufficient to generate a compound of the formula:
- R--O--CH.sub.2 (OCH.sub.2).sub.x OR (V)
- wherein x is between 1 and 5;
- (b) reacting the product of (V) with a carboxylic acid anhydride having between about 2 to about 8 carbon atoms for a time and at a temperature sufficient to generate the compound of formula (I).
A process of producing a compound containing an acyloxyalkoxy group from an alcohol which comprises:
- (a) reacting the alcohol of the formula R--OH wherein R is an organic moiety with a formaldehyde donor in the presence of a catalyst for a time and at a temperature sufficient to generate a compound of the formula:
- R--O--CH.sub.2 (OCH.sub.2).sub.x OR (V)
- wherein x is between about 1 to about 5;
- and
- (b) reacting the compound of formula (V) with a carboxylic acid anhydride of the formula (R.sup.1 CO).sub.2 O wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group for a time and at a temperature sufficient to generate a compound of the formula:
- R--O--CH.sub.2 O--COR.sup.1.
Dependencies are inferred from the claim text.