Sulfuric Acid → Isopropyl 2-iodo-5-methylphenylacetate

HRID 2087049Notes

Reaction equation

HRID 2087049 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[CH:18](O)([CH3:20])[CH3:19]>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH:18]([CH3:20])[CH3:19])=[O:11]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 219386462-Iodo-5-methylbenzeneacetic acid

Product 1

HCID 53789940Isopropyl 2-iodo-5-methylphenylacetate

Procedure

2-Iodo-5-methylphenylacetic acid (20.0 g, 72 mmol) and a catalytic amount of 98% sulfuric acid (0.2 ml) are dissolved in isopropyl alcohol (200 ml) and heated to reflux temperature for 48 hours. The solvent is removed on a rotovap and the residual oil partitioned between EtOAc (500 ml) and saturated NaHCO3 solution (500 ml). The organic layer is separated, dried (MgSO4) and concentrated on a rotovap. The residual oil is distilled using a kugelrohr apparatus to give a clear, colorless oil which solidifies on standing at room temperature to give isopropyl 2-iodo-5-methylphenylacetate, m.p. 48-500.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 48 hours
  3. customThe solvent is removed on a rotovap
  4. customthe residual oil partitioned between EtOAc (500 ml) and saturated NaHCO3 solution (500 ml)
  5. customThe organic layer is separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated on a rotovap
  8. distillationThe residual oil is distilled
  9. customto give a clear, colorless oil which
  10. customon standing at room temperature

Sources & evidence

ORD record
ord-2675f5baa8d545e0af1caeaea64c2877
Source dataset
uspto-grants-2004_04
Patent number
US06727281B2

Reaction notes

Loading…