Hydrochloric Acid → 2-(2-Isopropyl-5-indanyl)propionic acid

HRID 435972

Reaction equation

HRID 435972 reaction equation
[CH:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([CH:13]([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:10]=2)[C:5]1=O)([CH3:3])[CH3:2].Cl.O1CCOCC1>O>[CH:1]([CH:4]1[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=2)[CH2:12]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 126278922-(2-Isopropyl-1-oxoindan-6-yl)propionic acid

Product 1

HCID 687692-(2-Isopropyl-5-indanyl)propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15g. of 2-(2-isopropyl-1 -oxoindan-6-yl)propionic acid, 40g. of zinc amalgam, 50 ml. of conc. hydrochloride acid, 200 ml. of dioxane and 30 ml. of water was heated under reflux for 15 hours. After completion of the reaction, the reaction mixture was extracted with ether and the ether extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off from the extract and the residue was recrystallized from n-hexane to give 9.5g. of the desired product as colorless crystals of m.p. 90° - 91.5° C.

Workup

  1. temperatureunder reflux for 15 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with ether
  4. extractionthe ether extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off from the
  8. extractionextract
  9. customthe residue was recrystallized from n-hexane
  10. customto give 9.5g

Sources & evidence

ORD record
ord-679964d845704a9f8f13557841ed8dc5
Source dataset
uspto-grants-1977_02
Patent number
US04007179

Linked notes

Loading…