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US 4,734,516 AGranted
Process for the preparation of partially halogenated 1-propanols
AssigneeCiba-Geigy Corporation
InventorRobert W. Lang
Life of this patent
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Abstract
The reaction of a zinc compound compound of formula III CF.sub.3 CCl.sub.2 ZnCl.yL (III) wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula II R--CHO (II) wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.
Claims16
A process for the preparation of a partially halogenated 1-propanol of the formula ##STR7## comprising reacting an aldehyde of the formula
- R--CHO (II)
- in an inert solvent with a zinc compound of the formula
- CF.sub.3 CCl.sub.2 Z.sub.n Cl.yL (III),
- with the exception of the reaction of CF.sub.3 CCl.sub.3 and an aldehyde of formula II in the presence of zinc, and isolating the resultant 1-propanol of formula I;
- wherein
- y is one or two;
- L is a solvent ligand selected from an N-disubstituted acid amide, an N-substituted lactam, and an organic sulfoxide;
- and
- R is a hydrogen atom;
- an unsubstituted or substituted, aliphatic or aromatic, hydrocarbon radical of 1-30 carbon atoms;
- each of said aliphatic radicals being uninterrupted or interrupted by --C(O)-- or --C(O)O--;
- said substituents of the R radical being selected from C.sub.1-18 alkyl, C.sub.2-18 alkenyl, C.sub.2-18 alkynyl, C.sub.6-18 aryl, C.sub.7-18 aralkyl, C.sub.7-18 alkaryl, C.sub.8-18 alkarylalkyl, C.sub.1-8 alkoxy, C.sub.1-8 alkylthio, C.sub.6-18 aryloxy, C.sub.7-18 aralkoxy, C.sub.7-18 aralkylthio, C.sub.6-8 aryloxy, C.sub.7-18 aralkoxy, C.sub.7-18 aralkylthio, C.sub.7-18 alkaryloxy, C.sub.8-18 alkarylalkoxy, C.sub.7-18 aryloxyarlkyl, C.sub.7-18 alkoxyaryl, C.sub.3-12 cycloalkyl, C.sub.3-12 cycloalkoxy, C.sub.3-12 cycloalkenyl, C.sub.3-12 cycloalkenyloxy, --COOH, --CONH.sub.2, --COOR.sup.1, --CONHR.sup.1, --CONR.sup.1 R.sup.2, --CN, --OH, --SH, --SO.sub.2 H, --SO.sub.3 H, --SO.sub.2 R.sup.1, --SO.sub.3 R.sup.1, --PO.sub.2 H, --PO.sub.3 H.sub.2, --PO.sub.2 R.sup.1, --PO.sub.3 R.sup.1, --NO.sub.2, --NH.sub.2, --NHR.sup.1, --NR.sup.1 R.sup.2, F, Cl, Br, I, and --NCO;
- R.sup.1 and R.sup.2 independently being selected from C.sub.1-18 alkyl, cyclohexyl, phenyl, or benzyl;
- said substituents on R being unsubstituted or further substituted by halogen, hydroxy, carboxy, cyano, or methoxy carbonyl.
11 more elements
Dependencies are inferred from the claim text.