Hydrochloric Acid → 3-Isopropoxybenzoic acid

HRID 1683073Notes

Reaction equation

HRID 1683073 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].I[CH:12]([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].Cl>O.CC(=O)CC>[CH:12]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 74203-Hydroxybenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 5867093-Isopropoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Combine 3-hydroxybenzoic acid (100 mmol), 2-iodopropane (500 mmol), K2CO3 (300 mmol), and 2-butanone (300 mL). Heat at reflux for 72 h. Concentrate in vacuo to obtain a residue. Add water (500 mL) and cool in an ice bath. Adjust to pH 1 by dropwise addition of concentrated HCl. Extract with dichloromethane (3×200 mL). Extract the combined organic layers with water (200 mL), dry over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Purify to obtain the title compound.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 72 h
  3. concentrationConcentrate in vacuo
  4. customto obtain a residue
  5. extractionExtract with dichloromethane (3×200 mL)
  6. extractionExtract the combined organic layers with water (200 mL)
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customto obtain a residue
  11. customPurify

Sources & evidence

ORD record
ord-927ee306d66b44d6a96177cb691e85b8
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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