Methanol → Methyl 4-(4-iodophenyl)butanoate

HRID 968819

Reaction equation

HRID 968819 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:19]O>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:19])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 46454274-(p-Iodophenyl)butyric acid

Product 1

HCID 11403935Methyl 4-(4-iodophenyl)butanoate

Procedure

To a solution of 4-(p-iodophenyl)-butyric acid (45.0 g, 0.155 mol) in methanol (1.3 L), was added sulfuric acid (concentrated, 8.4 mL) dropwise and it was stirred at room temperature under nitrogen for 3 hours. The reaction mixture was concentrated on a rota-vapor, the residue was then partitioned between ethyl acetate (700 mL) and saturated sodium bicarbonate aqueous solution (500 mL). The organic phase was separated, washed with brine (2×200 mL), then dried over Na2SO4 and filtered. Evaporation of solvent gave the titled compound as an oil that was used in step B without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated on a rota-vapor
  2. customthe residue was then partitioned between ethyl acetate (700 mL) and saturated sodium bicarbonate aqueous solution (500 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (2×200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-ead1684ac2394d2d999f52d4ee7a9e11
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Linked notes

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