Potassium Hydroxide → 2-Acetylhexanoic Acid

HRID 890697Notes

Reaction equation

HRID 890697 reaction equation
[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([O:7]C)=[O:6])(=[O:3])[CH3:2].[OH-].[K+]>O1CCOCC1>[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([OH:7])=[O:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12527573Methyl 2-acetylhexanoate

Product 1

HCID 193527442-Acetylhexanoic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

3.08 g (17.9 mmol) of methyl 2-acetylhexanoate (Example 14A) is dissolved in 10 ml of dioxane and cooled to 0° C. 7.00 ml of a 3.5 M potassium hydroxide solution are added with cooling. After a reaction time of 5 h, the batch is concentrated, treated with 20 ml of ethyl acetate and 20 ml of water and extracted with shaking. The water phase is recovered, cooled to 0° C. and slowly treated with 1 N hydrochloric acid until a pH of 1 is reached. The mixture is then extracted with dichloromethane. The dichloromethane phase is dried and directly reacted further without concentrating.

Workup

  1. temperaturewith cooling
  2. concentrationAfter a reaction time of 5 h, the batch is concentrated
  3. additiontreated with 20 ml of ethyl acetate and 20 ml of water
  4. extractionextracted
  5. customThe water phase is recovered
  6. temperaturecooled to 0° C.
  7. additionslowly treated with 1 N hydrochloric acid until a pH of 1
  8. extractionThe mixture is then extracted with dichloromethane
  9. dry with materialThe dichloromethane phase is dried
  10. customdirectly reacted further
  11. concentrationwithout concentrating

Sources & evidence

ORD record
ord-5409eda4de874948a53cf7564bc55c07
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

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