Sodium Hydroxide → 2-(4-{[(Prop-2-en-1-yloxy)carbonyl]amino}phenoxy)acetic acid

HRID 1089128Notes

Reaction equation

HRID 1089128 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:15]([O:18][C:19](Cl)=[O:20])[CH:16]=[CH2:17]>O>[CH2:15]([O:18][C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1)=[O:20])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 957972-(4-Aminophenoxy)acetic acid

Product 1

HCID 221604452-(4-{[(Prop-2-en-1-yloxy)carbonyl]amino}phenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.9 g of 4-aminophenoxyacetic acid is suspended in 15 ml of water, and 2.4 ml of 5N NaOH solution are added. After cooling with ice, 0.63 ml of chloroformic acid allyl ester is added over a period of 5 minutes. After removing the cooling bath, the reaction mixture is stirred for 20 minutes at room temperature. The reaction mixture is then washed twice with ethyl acetate, and the aqueous phase is adjusted to pH 2 with 4N HCl and extracted with ethyl acetate. The organic solution is washed with brine and dried over sodium sulphate. The title compound is obtained after evaporating off the solvent.

Workup

  1. additionis added over a period of 5 minutes
  2. customAfter removing the cooling bath
  3. washThe reaction mixture is then washed twice with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic solution is washed with brine
  6. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-11fb873d26a5404b9b34d4325c34d3d5
Source dataset
uspto-grants-1990_10
Patent number
US04965260

Reaction notes

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