Methanol → HCID 68690903, compound

HRID 1160386Notes

Reaction equation

HRID 1160386 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([OH:11])=[O:10].[OH-].[K+].CO.[N+:17]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26]Br)=[CH:22][CH:21]=1)([O-:19])=[O:18]>CN(C)C=O>[N+:17]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneHCID 15075538533931-68-9

Product 1

HCID 68690903HCID 68690903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 g (0.15 M) of 2-hydroxyphenylpropanoic acid and 16.9 g (0.12 M) of potassium hydroxide are added to a mixture of 150 ml of methanol and 20 ml of dimethylformamide in a 1000 ml reactor. After stirring for 10 minutes, 30 g (0.15 M) of 2-(4-nitrophenoxy)ethyl bromide are added and the reaction medium is then refluxed for 24 hours with stirring. The methanol is evaporated off and the residue is taken up in water. The aqueous phase obtained is first washed with ethyl acetate and then acidified with dilute aqueous hydrochloric acid and extracted with ethyl acetate.

Workup

  1. temperaturethe reaction medium is then refluxed for 24 hours
  2. stirringwith stirring
  3. customThe methanol is evaporated off
  4. customThe aqueous phase obtained
  5. washis first washed with ethyl acetate
  6. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-4102835cc97c4be6adf4d31a2dbd1899
Source dataset
uspto-grants-2010_10
Patent number
US07816397B2

Reaction notes

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