Methyl 4-allyl-3-hydroxyoctanoate → HCID 86646127, compound

HRID 551631Notes

Reaction equation

HRID 551631 reaction equation
[CH2:1]([CH:4]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:5]([OH:11])[CH2:6][C:7]([O:9]C)=[O:8])[CH:2]=[CH2:3]>[OH-].[K+].CO>[CH2:1]([CH:4]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:5]([OH:11])[CH2:6][C:7]([OH:9])=[O:8])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 86646126Methyl 4-allyl-3-hydroxyoctanoate

Product 1

HCID 86646127HCID 86646127, compound

Reagents, catalysts & solvents 1

HCID 23689386Potassium hydroxide methanolSolvent

Procedure

Methyl 4-allyl-3-hydroxyoctanoate (6.8 g, 31.7 mmol) was dissolved in a 2 N potassium hydroxide-methanol solution (20 mL), and the solution was stirred overnight at room temperature. The reaction solution was concentrated, then diluted with water, and washed with ether. The aqueous solution was made acidic using hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain the compound of interest as an oil substance (6.0 g, 30 mmol). This compound was used in the next reaction without being purified.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with water
  3. washwashed with ether
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customto obtain the compound of interest as an oil substance (6.0 g, 30 mmol)
  9. customThis compound was used in the next reaction
  10. customwithout being purified

Sources & evidence

ORD record
ord-1189e0f8b36044f3973376ec231a3191
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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