4-([6-(TETRAHYDRO-2H-PYRAN-2-YLOXY)HEXYL]OXY)BENZENECARBOXYLIC ACID synthesis
- Product Name:4-([6-(TETRAHYDRO-2H-PYRAN-2-YLOXY)HEXYL]OXY)BENZENECARBOXYLIC ACID
- CAS Number:201601-60-7
- Molecular formula:C18H26O5
- Molecular Weight:322.4
Yield:201601-60-7 1.7 kg
Reaction Conditions:
with toluene-4-sulfonic acid in tetrahydrofuran at 50; for 48 h;
Steps:
10.3
To a reaction flask containing 6500 mL of tetrahydrofuran (THF) was added TsOH (17.13 g, 0.09 mol) and 4-((6-hydroxyhexyl)oxy)benzoic acid. The resulting suspension was stirred at room temperature and dihydropyran (984 ml, 10.80 mol) was added drop-wise over one hour, then heated to 50° C. After stirring for 24 hours at this temperature, dihydropyran (654 ml, 7.17 mol) was added dropwise over one hour and the reaction mixture was stirred at 50° C. for 24 hours. (0269) The solution was cooled to room temperature, filtered through diatomaceous earth then concentrated. The recovered product was dissolved in 9000 ml of methylene chloride, again filtered through diatomaceous earth, then concentrated and poured into 9000 ml of petroleum ether. The precipitate thus formed was collected by filtration and purified by recrystallization in petroleum ether and dried in vacuum to yield a white solid (1.70 Kg). NMR showed that the product had a structure consistent with 4-((6-((tetrahydro-2H-pyran-2-yl)oxy)hexyl)oxy)benzoic acid.
References:
US2017/275534,2017,A1 Location in patent:Paragraph 0268
53963-10-3
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