Sodium Hydroxide → 2-Acetyl-5-phenylpentanoic acid

HRID 1368291Notes

Reaction equation

HRID 1368291 reaction equation
[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7]C)=[O:6])(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:5]([OH:7])=[O:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11333780Methyl 2-acetyl-5-phenylpentanoate

Product 1

HCID 219353022-Acetyl-5-phenylpentanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

1.00 g (4.45 mmol) of methyl 2-acetyl-5-phenylpentanoate is dissolved in 10 ml of dioxane and cooled to 0° C. 8.5 ml of a 1 M sodium hydroxide solution are added with cooling. After a reaction time of 5 h, the batch is concentrated, treated with 10 ml of ethyl acetate and 10 ml of water and extracted by shaking. The water phase is recovered, cooled to 0° C. and slowly treated with 1 N hydrochloric acid with cooling until pH 1 is reached. It 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 10 ml of ethyl acetate and 10 ml of water
  4. extractionextracted
  5. customThe water phase is recovered
  6. temperaturecooled to 0° C.
  7. additionslowly treated with 1 N hydrochloric acid
  8. temperaturewith cooling until pH 1
  9. extractionIt is then extracted with dichloromethane
  10. dry with materialThe dichloromethane phase is dried
  11. customdirectly reacted further
  12. concentrationwithout concentrating

Sources & evidence

ORD record
ord-5dd81e8c02524b8d93086ac16c8a51f5
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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