Lithium hydroxide, monohydrate → 3-(4-Nitrophenoxy)benzoic acid

HRID 78317

Reaction equation

HRID 78317 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:5])C.C1COCC1.O.O[Li].O>O>[C:4]([C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)[O:9][C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 11323654Ethyl 3-(4-nitrophenoxy)benzoateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 7679193-(4-Nitrophenoxy)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a vigorously stirred mixture of 4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene (5.14 g, 17.9 mmol) in a 3:1 THF/water solution (75 mL) was added a solution LiOH.H2O (1.50 g, 35.8 mmol) in water (36 mL). The resulting mixture was heated at 50° C. overnight, then cooled to room temp., concentrated under reduced pressure, and adjusted to pH 2 with a 1M HCl solution. The resulting bright yellow solids were removed by filtration and washed with hexane to give 4-(3-carboxyphenoxy)-1-nitrobenzene (4.40 g, 95%).

Workup

  1. temperaturecooled to room temp.
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting bright yellow solids were removed by filtration
  4. washwashed with hexane

Sources & evidence

ORD record
ord-7d682fa717ad412f9b24c6d02ddba9c3
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Linked notes

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