Ammonia → Phloretamide

HRID 2422221Notes

Reaction equation

HRID 2422221 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12]C)=O)=[CH:4][CH:3]=1.Cl.[NH3:15]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

HCID 16222514PhloretamideYield 31%

Procedure

25% Aqueous ammonia (30 mL) was added to methyl 4-hydroxybenzenepropanoate (1.5 g, 8.3 mmol), and the mixture was stirred at room temperature for 15 hrs. Dil. hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.43 g, yield 31%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-042e7e897e59462d954b9ab43f6338cc
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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