Sodium Hydroxide → 2-[(5-Chloropyridin-2-yl)oxy]-2-methylpropanoic acid

HRID 2104277Notes

Reaction equation

HRID 2104277 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>C(#N)C.O>[CH3:8][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 16098339Ethyl 2-[(5-chloropyridin-2-yl)oxy]-2-methylpropanoate

Product 1

HCID 160983412-[(5-Chloropyridin-2-yl)oxy]-2-methylpropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 2-methyl-2-(5-chloro-2-pyridyloxy)propionate and sodium hydroxide (0.85 g, 21 mmol) in 15 mL of acetonitrile and 15 mL of water was heated at 50° C. overnight. The volatile materials were removed by concentrating on a rotary evaporator, and the residue was partitioned between 2 M hydrochloric acid (100 mL) and ether (100 mL). The organic layer was separated and washed with water (2×50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.02 (d, 1H), 7.65 (dd, 1H), 6.77 (d, 1H), 1.62 (s, 6H). LC-MS: m/e 216 (M+H)+ (2.33 min).

Workup

  1. customThe volatile materials were removed
  2. concentrationby concentrating on a rotary evaporator
  3. customthe residue was partitioned between 2 M hydrochloric acid (100 mL) and ether (100 mL)
  4. customThe organic layer was separated
  5. washwashed with water (2×50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-82b2981a2427408488ebbaa32b342b3d
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

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