Acetone → Isopropyl 2-(3-isopropoxyphenyl)acetate

HRID 2269854Notes

Reaction equation

HRID 2269854 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:12](I)([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[CH3:22][C:23]([CH3:25])=O>>[CH:12]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH:23]([CH3:25])[CH3:22])[CH:3]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 54166898Isopropyl 2-(3-isopropoxyphenyl)acetate

Procedure

Combine 3-hydroxy-phenylacetic acid (9.26 g, 60.9 mmol), isopropyl iodide (42.6 g, 250 mmol), and acetone (80 mL). Add portionwise, potassium carbonate (16.9 g, 122 mmol). Heat to reflux with vigorous mechanical stirring. After 20 hours, cool to ambient temperature and evaporate in vacuo to give a residue. Partition the residue between diethyl ether and 5% sodium hydroxide solution. Extract the organic layer with water and a saturated sodium chloride solution. Dry the organic layer over MgSO4, filter and evaporate in vacuo to obtain a liquid. Bulb-to-bulb distillation gives 3-isopropoxy-phenyl-acetic acid isopropyl ester: bp; 125° C. at 0.2 mm of Hg.

Workup

  1. additionAdd portionwise
  2. temperatureHeat
  3. temperatureto reflux with vigorous mechanical stirring
  4. customevaporate in vacuo
  5. customto give a residue
  6. customPartition the residue between diethyl ether and 5% sodium hydroxide solution
  7. extractionExtract the organic layer with water
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto obtain a liquid
  12. distillationBulb-to-bulb distillation

Sources & evidence

ORD record
ord-e56d52477849487cb31120c613e2b695
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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