Water → Methyl 3-(3-methoxyphenyl)butanoate

HRID 2052604Notes

Reaction equation

HRID 2052604 reaction equation
[CH3:1][Li].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11].O>CCOCC>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]([CH3:1])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 54105512Methyl m-methoxycinnamateHCID 178418348HCID 178418348, compound

Product 1

HCID 20376239Methyl 3-(3-methoxyphenyl)butanoateYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a N2 blanket, a solution of lithium dimethylcuprate was prepared at 0° C. from cuprous iodide (7.6 g, 0.04 mol) and a solution of methyl-lithium in ether (80 ml, 1 M, 0.08 mol). A solution of methyl m-methoxycinnamate (4.8 g, 0.025 mol) in ether (20 ml) was then added dropwise and the reaction mixture was stirred for 1 hour at 0° C. A large volume of water was cautiously added, after which the ether layer was separated, dried (anhydrous Na2SO4) and evaporated to dryness. The residue was chromatographed on silica gel (100 g) with hexane/ethyl acetate (80:20) as eluent, giving 3.65 g methyl β-(m-methoxyphenyl)-butyrate (68% yield by weight).

Workup

  1. customafter which the ether layer was separated
  2. dry with materialdried (anhydrous Na2SO4)
  3. customevaporated to dryness
  4. customThe residue was chromatographed on silica gel (100 g) with hexane/ethyl acetate (80:20) as eluent

Sources & evidence

ORD record
ord-270f762b52754836b9a56a7cc5b79f60
Source dataset
uspto-grants-1980_01
Patent number
US04186142

Reaction notes

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