Methanol → 4-(4-Methoxyphenyl)butanoic acid methyl ester

HRID 968817Notes

Reaction equation

HRID 968817 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:20]O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:20])=[O:13])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 782804-(4-Methoxyphenyl)butyric acid

Product 1

HCID 1407254-(4-Methoxyphenyl)butanoic acid methyl esterYield 99%

Procedure

To a solution of 4-(4-methoxyphenyl)-butyric acid (25.1 g, 0.129 mol) in methanol (130 mL), was added sulfuric acid (concentrated, 1.0 mL) dropwise and it was stirred at room temperature overnight under nitrogen. The reaction mixture was concentrated on a rota-vapor, the residue was then partitioned between ethyl acetate (200 mL) and saturated sodium bicarbonate aqueous solution (200 mL). The organic phase was separated, washed with brine (3×200 mL), then dried over Na2SO4 and filtered. Evaporation of solvent gave the titled compound as an oil (26.8 g, 99%). Mass (MH+)=209.

Workup

  1. concentrationThe reaction mixture was concentrated on a rota-vapor
  2. customthe residue was then partitioned between ethyl acetate (200 mL) and saturated sodium bicarbonate aqueous solution (200 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (3×200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-d14a26b6d66c434ca24be2197d24a2a5
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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