Hydrochloric Acid → 4-Hydroxy-2,2-dimethylbutanoic acid

HRID 1806922Notes

Reaction equation

HRID 1806922 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:7][CH2:6][O:5][C:3]1=[O:4].[OH-:9].[K+].Cl>O>[OH:5][CH2:6][CH2:7][C:2]([CH3:8])([CH3:1])[C:3]([OH:9])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 947462,2-Dimethyl-4-butyrolactone

Product 1

HCID 138845934-Hydroxy-2,2-dimethylbutanoic acidYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step A A mixture of 2,2-dimethylbutyrolactone (6.84 g, 60 mmol) and KOH (3.36 g) in H2O (60 mL) was heated at reflux for 2 h. The solution was cooled to room temperature, and acidified to “pH” 5 with aqueous HCl solution. The mixture was then extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, concentrated under reduced pressure to give 4-hydroxy-2,2-dimethyl-butanoic acid as a colorless oil (4 g, 51%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionThe mixture was then extracted with ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e10b4c15f28147b4b4ca7ddc56483c6f
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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