Sulfuric Acid → tert-Butyl 4-iodobutanoate

HRID 2227885Notes

Reaction equation

HRID 2227885 reaction equation
S(=O)(=O)(O)O.[I:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[CH2:13]=[C:14]([CH3:16])[CH3:15].C(=O)(O)[O-].[Na+]>O1CCOCC1>[I:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][C:14]([CH3:16])([CH3:15])[CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 33547744-Iodobutyric acid

Product 1

HCID 12416448tert-Butyl 4-iodobutanoateYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of concentrated sulfuric acid (2 ml) and 1,4-dioxane (20 ml) in a pressure bottle at 0° C. were added 4-iodobutanoic acid (5.5 g, 25.7 mmol) and isobutene (30 ml). The mixture was stirred at room temperature for 3 days, cooled to 0° C. and poured slowly into an aqueous solution (120 ml) of sodium bicarbonate (10 g). The mixture was stirred at room temperature for 15 minutes and extracted with diethyl ether. The organic phase was washed three times with brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane:dichloromethane=1:1) to give the title compound (4.24 g, 61%) as a pale yellow liquid.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe mixture was stirred at room temperature for 15 minutes
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed three times with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (hexane:dichloromethane=1:1)

Sources & evidence

ORD record
ord-443143343b134bad88b1a662b6d1fc45
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

Loading…