ChemicalBook CAS DataBase List 4,5-DIMETHYLBENZENE-1,2-DIMETHANOL

4,5-DIMETHYLBENZENE-1,2-DIMETHANOL synthesis

6synthesis methods

Product Name:4,5-DIMETHYLBENZENE-1,2-DIMETHANOL
CAS Number:60070-05-5
Molecular formula:C10H14O2
Molecular Weight:166.22

17649-59-1
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60070-05-5
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Yield:60070-05-5 100%

Reaction Conditions:

Stage #1: dimethyl 4,5-dimethylphthalatewith lithium aluminium tetrahydride in tetrahydrofuran at -78 - 20;Reflux;
Stage #2: with phosphorus tribromide

Steps:

3

Preparation of 1,2-bis(bromomethyl)-4,5-dimethylbenzene Dried tetrahydrofurane (20 mL) was put into LAH (0.54 g, 14.29 mmol) at -78° C. Dimethyl 4,5-dimethylbenzene-1,2-dicarboxylate (1.27 g, 5.71 mmol) was dissolved in dried tetrahydrofurane (10 mL), and then the resultant mixture was slowly added into the above reaction solution. Then the reaction temperature was slowly raised to room temperature, and then stirring under reflux was performed for 24 hours. After the reaction, the resultant reaction material was cooled by a sodium hydroxide solution, and then concentrated under reduced pressure, followed by washing with ethyl acetate twice and again washing with distilled water once. The organic layer was separated, and dried over sodium sulfate, and then the solvent was concentrated under reduced pressure, thereby obtaining white solids, (4,5-dimethyl-1,2-phenylene)dimethanol (0.95 g, quantitative). This is subjected to a bromination reaction using tribromophosphine, thereby obtaining 1,2-bis(bromomethyl)-4,5-dimethyl benzene at a yield of 56%. ¹H-NMR 300 MHz (CDCl₃) δ 7.13 (s, 2H), 4.27 (s, 4H), 2.23 (s, 6H).

References:

US2012/4476,2012,A1 Location in patent:Page/Page column 9

5999-20-2 Synthesis