Acetone → Ethyl 4-iodobutanoate

HRID 1614056Notes

Reaction equation

HRID 1614056 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CC(C)=O.[I-:14].[Na+]>C(Cl)Cl>[I:14][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 18474Ethyl 4-chlorobutyrate

Product 1

HCID 10890062Ethyl 4-iodobutanoateYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix ethyl 4-chlorobutyrate (80 g), acetone (400 mL) and sodium iodide (100 g). Reflux for 8 hours, cool and add methylene chloride (400 mL). Filter and evaporate the filtrate to a residue. Partition the residue between methylene chloride (200 mL) and water (200 mL). Separate the organic phase, dry (MgSO4) and evaporate to an oil. Purify by distillation to give the title compound (89 g); bp 64° [email protected] mm Hg.

Workup

  1. temperatureReflux for 8 hours
  2. temperaturecool
  3. filtrationFilter
  4. customevaporate the filtrate to a residue
  5. customPartition the residue between methylene chloride (200 mL) and water (200 mL)
  6. customSeparate the organic phase
  7. dry with materialdry (MgSO4)
  8. customevaporate to an oil
  9. distillationPurify by distillation

Sources & evidence

ORD record
ord-9ef6f01f00834f6893f79213c5bea678
Source dataset
uspto-grants-1993_03
Patent number
US05194430

Reaction notes

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