Methyl 2-(3-methoxyphenyl)-2-methylpropanoate → 2-(3-Methoxyphenyl)-2-methylpropanoic acid

HRID 2071051Notes

Reaction equation

HRID 2071051 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:15])([CH3:14])[C:10]([O:12]C)=[O:11])[CH:6]=[CH:7][CH:8]=1>C1COCC1.CO.[Li+].[OH-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:15])([CH3:14])[C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 1

HCID 21883537Methyl 2-(3-methoxyphenyl)-2-methylpropanoate

Product 1

HCID 108216342-(3-Methoxyphenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 2-(3-methoxyphenyl)-2-methylpropanoate (800 mg, 4 mmol) in THF (10 ml) and MeOH (10 ml), aqueous LiOH (excess) was added and the reaction mixture was heated at 60° C. for 7 h. Then volatiles were removed in vacuum and the aqueous layer was extracted with ether. Ether layer was discarded. Then the aqueous layer was acidified and extracted with ethyl acetate. Organic layer was dried with sodium sulfate and volatiles removed under vacuum to yield 2-(3-methoxyphenyl)-2-methylpropanoic acid.

Workup

  1. customThen volatiles were removed in vacuum
  2. extractionthe aqueous layer was extracted with ether
  3. extractionextracted with ethyl acetate
  4. dry with materialOrganic layer was dried with sodium sulfate and volatiles
  5. customremoved under vacuum

Sources & evidence

ORD record
ord-9011ba58b0fe4d3f864549ea8fc8175d
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…