Sodium Hydroxide → 3,5-dimethyldodecanoic acid

Temperature

170 °C

In a nitrogen atmosphere, the crude product (41.6 g, 0.0899 mol) of ethyl 2-(1,3-dimethyldecyl)malonate (4Et) obtained in the method of Example 1-1 and a 13% by weight aqueous sodium hydroxide solution (87 g) were placed in a reaction vessel and stirred for one hour under refluxing with heating. Then ethanol thus generated therein was distilled off in one hour. The resulting mixture was subjected to addition of 20% by weight hydrochloric acid (87 g) and extracted with a mixture of toluene and tetrahydrofuran. The resulting organic phase was concentrated under reduced pressure, and then the residue was stirred under heat at 170° C. for 6 hours in a nitrogen atmosphere. This reaction mixture was diluted with tetrahydrofuran, washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The concentrate thus obtained was distilled under reduced pressure (bp 130 to 140° C./2 mmHg) to obtain 3,5-dimethyldodecanoic acid (5) (18.9 g, 0.0828 mol). A total yield of three steps from the 2-methylnonyl chloride (1Cl) was 67%.

1. temperatureunder refluxing
2. temperaturewith heating
3. distillationThen ethanol thus generated therein was distilled off in one hour
4. additionThe resulting mixture was subjected to addition of 20% by weight hydrochloric acid (87 g)
5. extractionextracted with a mixture of toluene and tetrahydrofuran
6. concentrationThe resulting organic phase was concentrated under reduced pressure
7. stirringthe residue was stirred
8. additionThis reaction mixture was diluted with tetrahydrofuran
9. washwashed with an aqueous saturated sodium chloride solution
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. concentrationThe concentrate thus
13. customobtained
14. distillationwas distilled under reduced pressure (bp 130 to 140° C./2 mmHg)

ORD record

ord-b3d2401952ff4266b88aedd44f04cd1d

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278900B2