Hydrochloric Acid → 4-(2,3-Dimethylphenoxy)butanoic acid

HRID 2175208Notes

Reaction equation

HRID 2175208 reaction equation
[CH3:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]CC)=[O:9].[Li+].[OH-].Cl>O1CCOCC1>[CH3:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57586544Ethyl 4-(2,3-dimethylphenoxy)butyrate

Product 1

HCID 16225244-(2,3-Dimethylphenoxy)butanoic acidYield 102.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 4-(2,3-dimethylphenoxy)butanoate (22.28 g, 94 mmol), 4 N LiOH (94 mL, 377 mmol) in dioxane (50 mL) was heated at 60° C. for 4 h. After cooling to room temperature, the mixture was adjusted to pH 2-3 with 3 N HCl, and extracted with EtOAc (2×10 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford the title compound (20 g, 100% yield). LCMS, [M−H]+=207.1. 1H NMR (400 MHz, CDCl3) δ 7.02 (dd, J=8.2, 7.5 Hz, 1H), 6.76 (d, J=7.5 Hz, 1H), 6.67 (d, J=8.2 Hz, 1H), 3.99 (t, J=6.0 Hz, 2H), 2.60 (t, J=7.3 Hz, 2H), 2.25 (s, 3H), 2.18-2.09 (m, 2H), 2.12 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (2×10 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-244c6fd587254a49aecfdf5198104f42
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…