Acetic Acid → (R)-(-)-2-propyloctanoic acid

HRID 2391036

Reaction equation

HRID 2391036 reaction equation
CS(O)(=O)=O.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(O[CH:17]([CH3:19])[CH3:18])(=O)C.[C:20]([OH:23])(=[O:22])C>O>[CH2:8]([C@H:9]([CH2:10][CH2:11][CH2:12][CH2:18][CH2:17][CH3:19])[C:20]([OH:23])=[O:22])[CH2:7][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6395Methanesulfonic AcidHCID 18406121n-Heptane isopropyl acetate

Product 1

HCID 208925(R)-(-)-2-propyloctanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
108.5 °C

Procedure

Under an argon atmosphere, the compound (100 g) produced in Reference Example 3 was dissolved in acetic acid (230 mL) at about 40° C. (inner temperature). A solution of methanesulfonic acid (130 g) in water (182 mL) was added to the above solution, then stirred at about 105-112° C. (inner temperature) for about 13 hours, and cooled to about 28° C. (inner temperature). Then, water (400 mL) and a mixture of n-heptane: isopropyl acetate (5:1) (500 mL) were added and the mixture was extracted. The organic layer was washed twice with water (400 mL) and concentrated to give (2R)-2-propyloctanoic acid having the following physicochemical properties (103 g, 99.3% e.e.).

Workup

  1. temperaturecooled to about 28° C. (inner temperature)
  2. additionwere added
  3. extractionthe mixture was extracted
  4. washThe organic layer was washed twice with water (400 mL)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-73ccc542e7174b7aa2f0aab166d67b5b
Source dataset
uspto-grants-2012_09
Patent number
US08273916B2

Linked notes

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