Hydrochloric Acid → 4-(2-Methoxyethoxy)benzoic acid

HRID 523326Notes

Reaction equation

HRID 523326 reaction equation
[OH-].[K+].[CH3:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1.O.Cl>CCO>[CH3:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 20110213HCID 20110213, compound

Product 1

HCID 64855624-(2-Methoxyethoxy)benzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.3 g (64.95 mmol) of potassium hydroxide are added to a solution of 6.1 g (29 mmol) of methyl 4-(2-methoxyethoxy)benzoate in 100 mL of EtOH. The solution is heated up to reflux for one hour and poured onto icy water and acidified with a 25% HCl solution. The mixture is filtered off and washed 2 times with 100 mL of water. The solid is suspended in 100 ml of acetonitrile for 1 hour and the precipitate is filtered off and dried under pressure to yield 3.9 g (70%) of pure 4-(2-methoxyethoxy)benzoic acid as a white powder.

Workup

  1. temperatureThe solution is heated up
  2. temperatureto reflux for one hour
  3. filtrationThe mixture is filtered off
  4. washwashed 2 times with 100 mL of water
  5. filtrationthe precipitate is filtered off
  6. customdried under pressure

Sources & evidence

ORD record
ord-516d39fd426b4a82a35c4e2dc9f6f3dd
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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