Hydrochloric Acid → Ethyl 2,2-dimethylbutanoate

HRID 2047642Notes

Reaction equation

HRID 2047642 reaction equation
Cl.[CH3:2][C:3]([CH3:9])([CH2:7][CH3:8])[C:4]([OH:6])=[O:5].O.[CH2:11](O)[CH3:12]>>[CH2:11]([O:5][C:4](=[O:6])[C:3]([CH3:9])([CH3:2])[CH2:7][CH3:8])[CH3:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 116842,2-Dimethylbutanoic acid

Product 1

HCID 12647075Ethyl 2,2-dimethylbutanoate

Procedure

Add 0.2 mL of concentrated hydrochloric acid to 2,2-dimethyl-butanoic acid (5.0 g, 43.0 mmol) in ethanol (43 mL) and heat to reflux for 5 hours. Cool to room temperature. Pour the reaction into water and extract with diethyl ether. Wash the combined organics with saturated aqueous sodium bicarbonate and water, dry over magnesium sulfate, filter, and concentrate under reduced pressure to afford the title compound which was used without further purification (4.0 g, 64.4%): 1H NMR (CDCl3) δ 0.82 (t, 3H, 1.14 (s, 3H), 1.23 (t, 3H), 1.55 (q, 2H), 4.1 (q, 2H).

Workup

  1. temperatureheat
  2. temperatureto reflux for 5 hours
  3. additionPour
  4. extractionextract with diethyl ether
  5. washWash the combined organics with saturated aqueous sodium bicarbonate and water
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-59e87af6c13d4a4197ab5e5aa2efb6b9
Source dataset
uspto-grants-2013_11
Patent number
US08592590B2

Reaction notes

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