Isopropanol → Isopropyl 4-fluorophenylacetate

HRID 1709002Notes

Reaction equation

HRID 1709002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][CH:13](O)[CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH:13]([CH3:14])[CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 98372-(4-Fluorophenyl)acetic acid

Product 1

HCID 23038995Isopropyl 4-fluorophenylacetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-fluorophenylacetic acid (123.0 g), 2-propanol (96.0 g), p-toluenesulphonic acid (9.6 g) and benzene (1.3 g) is refluxed for 7 hours with a Dean-Stark separator. The solution is washed with a 10% aqueous solution of sodium carbonate (2×500 ml) and with water (2×500 ml). After drying over magnesium sulphate, the solvent and the excess 2-propanol are evaporated in vacuo. The residue is distilled (51°-53° /3.10 -2 Torr) to yield isopropyl 4-fluorophenylacetate.

Workup

  1. temperatureis refluxed for 7 hours with a Dean-Stark separator
  2. washThe solution is washed with a 10% aqueous solution of sodium carbonate (2×500 ml) and with water (2×500 ml)
  3. dry with materialAfter drying over magnesium sulphate
  4. customthe solvent and the excess 2-propanol are evaporated in vacuo
  5. distillationThe residue is distilled (51°-53° /3.10 -2 Torr)

Sources & evidence

ORD record
ord-cde81e637b1742bca7dc2df378c27ed8
Source dataset
uspto-grants-1990_08
Patent number
US04946861

Reaction notes

Loading…