Hydrochloric Acid → methyl 2-bromododecanoate

Initially, α-bromolauric acid methyl ester was prepared as follows. Pure lauric acid (100 gm 0.5 mol) was dissolved in thionyl chloride (89 gm, 0.75 mol) at 55° C. under nitrogen. A large amount of hydrogen chloride gas was generated. When all the lauric acid was converted to acid chloride and there was no more HCl gas being generated after stirring for 2.5 hours, bromine (89.25 gm, 0.65 mol) was slowly added to the solution at room temperature. The reaction mixture was stirred for another 8 hours at 45° C. The reaction was then stopped by evaporating additional bromine at 80° C. by bubbling in nitrogen. The crude product, α-bromolauric acid chloride, was cooled to 0° under nitrogen. Pure methanol was then added very slowly to the acid chloride solution at 0° C. The temperature was not allowed to exceed 15° C. during this process. The final crude product, α-bromolauric acid methyl ester, was washed with water several times. The final product was extracted twice with hexane. The NMR results showed that the product was completely pure. The yield of the reaction was about 98% and may be summarized as follows: ##STR7## B. Preparation of Hydroquinone Bislauric Acid Methyl Ester (2)

1. stirringThe reaction mixture was stirred for another 8 hours at 45° C
2. customby evaporating additional bromine at 80° C.
3. customby bubbling in nitrogen
4. temperatureThe crude product, α-bromolauric acid chloride, was cooled to 0° under nitrogen
5. additionPure methanol was then added very slowly to the acid chloride solution at 0° C
6. customto exceed 15° C. during this process
7. washThe final crude product, α-bromolauric acid methyl ester, was washed with water several times
8. extractionThe final product was extracted twice with hexane
9. customThe NMR results

ORD record

ord-3005820db8d54f96b2b4b031485475d3

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05945393