Lithium Hydroxide → 4-(2-Fluoroethoxy)benzoic acid

HRID 643480Notes

Reaction equation

HRID 643480 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][CH:6]=1.[Li+].[OH-]>O1CCOCC1>[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10943448Methyl 4-(2-fluoroethoxy)benzoate

Product 1

HCID 513570934-(2-Fluoroethoxy)benzoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-(2-fluoroethoxy)benzoate (7.7 g, 38.85 mmol) in dioxane (100 mL) was added LiOH (2M, 39 mL). The reaction mixture was stirred at room temperature for 18 hours, and then concentrated in vacuo. The residue was dissolved in H2O (30 ml) and extracted with ether. Under cooling the aqueous was acidified with HCl (6N) and extracted with CHCl3. The organic extracts were dried over MgSO4. Evaporation and recrystallization from ethyl acetate and methylene chloride gave the title compound as a white solid (5 g, 71% yield); 1H NMR (400 MHz, DMSO-d6) δ 4.28 (m, 1H), 4.35 (m, 1H,) 4.68 (m, 1H), 4.80 (m, 1H), 7.04 (d, 2H), 7.89 (d, 2H); MS m/e (M−H)− 183.1; mp 203° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in H2O (30 ml)
  3. extractionextracted with ether
  4. temperatureUnder cooling the
  5. extractionextracted with CHCl3
  6. dry with materialThe organic extracts were dried over MgSO4
  7. customEvaporation and recrystallization from ethyl acetate and methylene chloride

Sources & evidence

ORD record
ord-01a503aa8ff7433cb456d190d3907701
Source dataset
uspto-grants-2010_04
Patent number
US07700602B2

Reaction notes

Loading…