Acetic Acid → 3,5-dimethyldodecanoic acid

HRID 922094Notes

Reaction equation

HRID 922094 reaction equation
[CH3:1][CH:2]([CH:13](C([O-])=O)[C:14]([O:16]CC)=[O:15])[CH2:3][CH:4]([CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(O)(=O)C.S(=O)(=O)(O)O>O>[CH3:1][CH:2]([CH2:3][CH:4]([CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 131734962HCID 131734962, compound

Product 1

HCID 569358013,5-dimethyldodecanoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, ethyl 2-(1,3-dimethyldecyl)malonate (4Et) (18.6 g, 0.0566 mol), acetic acid (40 g), water (20 g), and sulfuric acid (2 g) were placed in a reaction vessel and stirred for 48 hours under refluxing with heating while distilling off ethanol. The reaction mixture was diluted with tetrahydrofuran and water. The organic phase was washed with an aqueous saturated sodium chloride solution and concentrated under reduced pressure. The concentrate thus obtained was distilled under reduced pressure (bp: from 130° C. to 140° C./2 mmHg) to obtain 3,5-dimethyldodecanoic acid (5) (11.4 g, 0.0498 mol). A total yield of three steps from the 2-methylnonyl chloride (1Cl) was 59%.

Workup

  1. temperatureunder refluxing
  2. temperaturewith heating
  3. distillationwhile distilling off ethanol
  4. additionThe reaction mixture was diluted with tetrahydrofuran and water
  5. washThe organic phase was washed with an aqueous saturated sodium chloride solution
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe concentrate thus
  8. customobtained
  9. distillationwas distilled under reduced pressure (bp: from 130° C. to 140° C./2 mmHg)

Sources & evidence

ORD record
ord-c60eac7c63014c3f9e4d5b2e350b66d1
Source dataset
uspto-grants-2016_03
Patent number
US09278900B2

Reaction notes

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