Hydrochloric Acid → 3-(4-Benzyloxyphenyl)propionic acid

HRID 2422197Notes

Reaction equation

HRID 2422197 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoate

Product 1

HCID 5613723-(4-Benzyloxyphenyl)propionic acidYield 67.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of methyl 4-(phenylmethoxy)benzenepropanoate (0.60 g, 2.2 mmol) in methanol (20 mL) was added 2N aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at 60° C. for 15 hrs. 2N Hydrochloric acid (3 mL) 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 (0.38 g, yield 67%).

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-98577b9fc9ab43ceb4694dc6bfd59166
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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