Potassium Hydroxide → HCID 12456487, compound

HRID 1267677Notes

Reaction equation

HRID 1267677 reaction equation
[CH2:1]([CH:7]([C:13]([O:15]CC)=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+]>C(O)C>[CH2:11]([O:10][C:8]([CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:13]([OH:15])=[O:14])=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 79385Diethyl hexylmalonate

Product 1

HCID 12456487HCID 12456487, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of diethyl 2-hexylmalonate of Example 8 (244.36 g, 1.000 mol) in 25 mL of absolute ethanol in a 2-L, 3-necked Morton flask was added a solution of potassium hydroxide (59.9 g, 0.907 mol)(weight adjusted for 85% assay of commercial potassium hydroxide) in 450 mL of absolute ethanol dropwise via a 500-mL pressure-equalizing dropping funnel over 75 min. The funnel was washed with 25 mL of absolute ethanol. The reaction mixture was stirred for 2 h, and 300 mL of ethanol was then removed under reduced pressure. Water (500 mL) was added, and the mixture extracted with 500 mL of heptane to remove unreacted diethyl 2-hexylmalonate. The aqueous solution was acidified with 12 M HCl to pH 2 then extracted with 500 mL of heptane. The heptane solution was dried (MgSO4) and the solvent removed under reduced pressure to give 2-(ethoxycarbonyl)octanoic acid as a colorless oil. Traces of ethanol were removed by adding 20 mL of toluene to the crude product, followed by stripping of the solvent at 1 mm Hg of pressure with stirring. The yield was 190.9 g (0.8827 mol, 88.3% based on diethyl 2-hexylmalonate, 97% based on potassium hydroxide).

Workup

  1. customover 75 min
  2. washThe funnel was washed with 25 mL of absolute ethanol
  3. custom300 mL of ethanol was then removed under reduced pressure
  4. additionWater (500 mL) was added
  5. extractionthe mixture extracted with 500 mL of heptane
  6. customto remove unreacted diethyl 2-hexylmalonate
  7. extractionthen extracted with 500 mL of heptane
  8. dry with materialThe heptane solution was dried (MgSO4)
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-afd869c7cb9447738a99acb1c490752f
Source dataset
uspto-grants-2003_04
Patent number
US06552204B1

Reaction notes

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