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US 5,710,296 AGranted
Process for preparing phenyl esters
AssigneeThe Clorox Company
InventorsLaFayette D. Foland, Thomas B. Ottoboni
Life of this patent
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Abstract
A method for preparing phenyl esters in high yields under mild reaction conditions is provided. Particularly preferred phenyl esters prepared in accordance with the inventive method are alkanyloxy-benzene compounds having a C.sub.2-18 alkyl. The method is practiced by reacting a carboxylic acid with an acid halide either in the presence of or followed by the addition of a phenol.
Claims15
A method of preparing a phenyl ester, comprising:
- reacting an aliphatic or aromatic carboxylic acid having the structure ##STR4## where R.sub.1 is C.sub.1-20 alkyl or alkenyl or an aryl, with an acid halide having the structure ##STR5## where A is a halide, methoxy, ethoxy, or an electron withdrawing group having an O, N, or S heteroatom and B is a halide, to form an activated intermediate;
- and,
- exposing the activated intermediate to a phenol to form a phenyl ester having the structure ##STR6## where Y and Z are each H, SO.sub.3 M, CO.sub.2 M, SO.sub.4 M, OH, a halo substituent, --OR.sup.2, R.sup.3, NR.sub.3 .sup.4 X, and mixtures thereof, wherein M is an alkali metal or alkaline earth counterion, R.sup.2 of the OR.sup.2 substituent is C.sub.1-30 alkyl, R.sup.3 is C.sub.1-6 alkyl, R.sup.4 of the NR.sub.3 .sup.4 substituent is C.sub.1-30 alkyl, X is a counterion, and Y and Z can be the same or different.
A method of forming an alkanyloxybenzene comprising:
- providing a reaction mixture in an aprotic solvent, the reaction mixture having a linear alkyl C.sub.2-12 carboxylic acid, phenol and chloroactyl chloride admixed therein;
- heating the reaction mixture to between about 70.degree. C. to about 135.degree.;
- and,
- isolating an alkanyloxybenzene reaction product having the structure ##STR8## where R.sub.1 is C.sub.2-12 alkyl, Y and Z are each H, SO.sub.3 M, CO.sub.2 M, SO.sub.4 M, OH, a halo substituent, --OR.sup.2, R.sup.3 NR.sub.3 .sup.4 X and mixtures thereof, wherein M is an alkali metal or alkaline earth counterion, R.sup.2 of the OR.sup.2 substituent is C.sub.1-20 alkyl, R.sup.3 is C.sub.1-6 alkyl, R.sup.4 of the NR.sub.3.sup.4 substituent is C.sub.1-30 alkyl, X is a counterion, and Y and Z can be the same or different.
1 more element
Dependencies are inferred from the claim text.