Sodium Hydroxide → HCID 20524182, compound

HRID 1702995Notes

Reaction equation

HRID 1702995 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12]C)=[O:11])=[C:6]([C:16](=[O:26])[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=1>O1CCOCC1>[Cl:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[C:6]([C:16](=[O:26])[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20524223HCID 20524223, compound

Product 1

HCID 20524182HCID 20524182, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1 N aqueous solution of sodium hydroxide (35 ml.) was added to a solution of methyl 2-[4-chloro-2-(4-nitrobenzoyl)phenoxy]acetate (11.5 g.) in dioxane (60 ml.) and stirred at room temperature for 1.5 hours. Dioxane was distilled off under reduced pressure, and the residue was washed with ethyl acetate, adjusted to pH 1 with 10% hydrochloric acid and then extracted with ethyl acetate (each 400 ml. and 100 ml.). The extracts were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then concentrated under reduced pressure to a volume of about 100 ml. The precipitating crystals were collected by filtration to give 2-[4-chloro-2-(4-nitrobenzoyl)phenoxy]acetic acid (10.1 g.).

Workup

  1. distillationDioxane was distilled off under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. extractionextracted with ethyl acetate (each 400 ml
  4. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure to a volume of about 100 ml
  7. filtrationThe precipitating crystals were collected by filtration

Sources & evidence

ORD record
ord-d331a875b95b4f6c8afc179abb5b39e6
Source dataset
uspto-grants-1982_09
Patent number
US04350692

Reaction notes

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