A compound represented by formula I or II. X represents a mono substituent on a benzene ring, and is selected from —H, —I, —Br, —Cl, —F, —CN, an amino, and a derivative thereof; R.sub.1 is a C.sub.2-10 alkyl, C.sub.2-10 alkyl substituted by cyclopropane or fluorine, except n-butyl; and M is an amine ion or metal ion.

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

A compound represented by formula I or II. X represents a mono substituent on a benzene ring, and is selected from H, I, Br, Cl, F, CN, an amino, and a derivative thereof; R.sub.1 is a C.sub.2-10 alkyl, C.sub.2-10 alkyl substituted by cyclopropane or fluorine, except n-butyl; and M is an amine ion or metal ion.

The present invention relates to a metal compound of calixarene not containing sulfur and dispersible in oil, which can be partially salified, or neutral, or basic or overbased, said calixarene having general formula (I) in which: a) R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently selected from hydrogen, or a group containing carbon and hydrogen, or a group containing in addition to carbon and hydrogen also heteroatoms, provided that said heteroatoms are not sulfur; b) one of the two substituents R.sub.5 and R.sub.6 is hydrogen, while the other may be selected from hydrogen, or a linear or branched alkyl with a number of carbon atoms between 1 and 6, preferably methyl, ethyl, 1-propyl, 2-propyl, n-butyl, sec-butyl, more preferably methyl or ethyl; c) n is the number of units of the calixarene ring and is comprised in the range between 4 and 16, preferably between 5 and 12; said calixarene being characterized in that in at least one of the n units of the calixarene ring, at least one of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 contains at least one acid group of carboxylic type available for the reaction with a metal base, with the proviso that said acid group of carboxylic type is not contained in a unit of the calixarene ring derived from salicylic acid. ##STR00001##

The present invention relates to a metal compound of calixarene not containing sulfur and dispersible in oil, which can be partially salified, or neutral, or basic or overbased, said calixarene having general formula (I) in which: a) R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently selected from hydrogen, or a group containing carbon and hydrogen, or a group containing in addition to carbon and hydrogen also heteroatoms, provided that said heteroatoms are not sulfur; b) one of the two substituents R.sub.5 and R.sub.6 is hydrogen, while the other may be selected from hydrogen, or a linear or branched alkyl with a number of carbon atoms between 1 and 6, preferably methyl, ethyl, 1-propyl, 2-propyl, n-butyl, sec-butyl, more preferably methyl or ethyl; c) n is the number of units of the calixarene ring and is comprised in the range between 4 and 16, preferably between 5 and 12; said calixarene being characterized in that in at least one of the n units of the calixarene ring, at least one of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 contains at least one acid group of carboxylic type available for the reaction with a metal base, with the proviso that said acid group of carboxylic type is not contained in a unit of the calixarene ring derived from salicylic acid. ##STR00001##

A method for synthesizing 4-(Hydroxymethyl)benzoic acid using P-xylene (PX) as a raw material, including: dissolving PX in an organic solvent to undergo an oxidation reaction with an oxidizing agent under an action of an M-MOF catalyst; and after the oxidation reaction, performing a post-treatment to obtain the 4-(Hydroxymethyl)benzoic acid; wherein, the metal element M in the M-MOF catalyst is Fe, Cu, Cr, Mn, Cu/Fe, Cu/Cr, Cu/Mn, Fe/Mn, Cr/Fe or Cr/Mn. The by-product produced in the reaction process is little, the yield is high, and the separation is convenient. The acid-base neutralization is not required in the reaction process, reducing pollution. A one-step reaction is employed which has mild reaction conditions, short reaction time, low pollution and is convenient for industrialized mass production; and the obtained 4-(Hydroxymethyl)benzoic acid can be used for preparing medicines and liquid crystal materials having wide applications.

A method for synthesizing 4-(Hydroxymethyl)benzoic acid using P-xylene (PX) as a raw material, including: dissolving PX in an organic solvent to undergo an oxidation reaction with an oxidizing agent under an action of an M-MOF catalyst; and after the oxidation reaction, performing a post-treatment to obtain the 4-(Hydroxymethyl)benzoic acid; wherein, the metal element M in the M-MOF catalyst is Fe, Cu, Cr, Mn, Cu/Fe, Cu/Cr, Cu/Mn, Fe/Mn, Cr/Fe or Cr/Mn. The by-product produced in the reaction process is little, the yield is high, and the separation is convenient. The acid-base neutralization is not required in the reaction process, reducing pollution. A one-step reaction is employed which has mild reaction conditions, short reaction time, low pollution and is convenient for industrialized mass production; and the obtained 4-(Hydroxymethyl)benzoic acid can be used for preparing medicines and liquid crystal materials having wide applications.

A method for synthesizing 4-(Hydroxymethyl)benzoic acid using P-xylene (PX) as a raw material, including: dissolving PX in an organic solvent to undergo an oxidation reaction with an oxidizing agent under an action of an M-MOF catalyst; and after the oxidation reaction, performing a post-treatment to obtain the 4-(Hydroxymethyl)benzoic acid; wherein, the metal element M in the M-MOF catalyst is Fe, Cu, Cr, Mn, Cu Te, Cu/Cr, Cu/Mn, Fe/Mn, Cr/Fe or Cr/Mn. The by-product produced in the reaction process is little, the yield is high, and the separation is convenient. The acid-base neutralization is not required in the reaction process, reducing pollution. A one-step reaction is employed which has mild reaction conditions, short reaction time, low pollution and is convenient for industrialized mass production; and the obtained 4-(Hydroxymethyl)benzoic acid can be used for preparing medicines and liquid crystal materials having wide applications.

A method for synthesizing 4-(Hydroxymethyl)benzoic acid using P-xylene (PX) as a raw material, including: dissolving PX in an organic solvent to undergo an oxidation reaction with an oxidizing agent under an action of an M-MOF catalyst; and after the oxidation reaction, performing a post-treatment to obtain the 4-(Hydroxymethyl)benzoic acid; wherein, the metal element M in the M-MOF catalyst is Fe, Cu, Cr, Mn, Cu Te, Cu/Cr, Cu/Mn, Fe/Mn, Cr/Fe or Cr/Mn. The by-product produced in the reaction process is little, the yield is high, and the separation is convenient. The acid-base neutralization is not required in the reaction process, reducing pollution. A one-step reaction is employed which has mild reaction conditions, short reaction time, low pollution and is convenient for industrialized mass production; and the obtained 4-(Hydroxymethyl)benzoic acid can be used for preparing medicines and liquid crystal materials having wide applications.