Hydrochloric Acid → 4-Methoxyphenylacetic Acid

HRID 446806Notes

Reaction equation

HRID 446806 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.CO.O[Li].O.Cl>O.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 84174Ethyl 4-methoxyphenylacetateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 76904-Methoxyphenylacetic AcidYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-methoxyphenyl)acetate (5.0 g, 0.025 mol) in 2:2:1 MeOH:THF:H2O (50 mL) was added LiOH.H2O (5.14 g, 0.128 mol). The reaction mixture was stirred at RT for 16 h and concentrated in vacuo to obtain the crude product. The crude material was acidified with HCl (1N) to pH 2 and then the product was extracted with EtOAc (2×100 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated in vacuo to afford 2-(4-methoxyphenyl)acetic acid (4.05 g, 94%) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain the crude product
  3. extractionthe product was extracted with EtOAc (2×100 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47027f1b7f3a46369e23bed86f5f91c6
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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