Sodium Hydroxide → 3,5-dimethyldodecanoic acid

In a nitrogen atmosphere, ethyl 2-(1,3-dimethyldecyl)malonate (4Et) (35.2 g, 0.107 mol) and a 13% by weight aqueous sodium hydroxide solution (104 g) were placed in a reaction vessel and stirred under refluxing with heating for one hour. Then, the resulting ethanol therein was distilled off in one hour. A 56% by weight aqueous sulfuric acid solution (93 g) was added thereto and the resulting mixture was under refluxing with heating for 30 hours. The reaction mixture was diluted with tetrahydrofuran. The organic phase was washed three times with an aqueous saturated sodium chloride solution and concentrated under reduced pressure. The concentrate thus obtained was distilled under reduced pressure (bp: from 130 to 140° C./2 mmHg) to obtain 3,5-dimethyldodecanoic acid (5) (21.6 g, 0.0944 mol). A total yield of three steps from the 2-methylnonyl chloride (1Cl) was 59%.

1. temperatureunder refluxing
2. temperaturewith heating for one hour
3. distillationThen, the resulting ethanol therein was distilled off in one hour
4. additionA 56% by weight aqueous sulfuric acid solution (93 g) was added
5. temperatureunder refluxing
6. temperaturewith heating for 30 hours
7. additionThe reaction mixture was diluted with tetrahydrofuran
8. washThe organic phase was washed three times with an aqueous saturated sodium chloride solution
9. concentrationconcentrated under reduced pressure
10. concentrationThe concentrate thus
11. customobtained
12. distillationwas distilled under reduced pressure (bp: from 130 to 140° C./2 mmHg)

ORD record

ord-a4bfa82cfae84049b861b0f495f00fb7

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278900B2