Acetic Acid → 4,7-Dimethylindan

HRID 1195454Notes

Reaction equation

HRID 1195454 reaction equation
Cl.[CH3:2][C:3]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=O.C(O)(=O)C>[Zn].O>[CH3:12][C:9]1[CH:10]=[CH:11][C:3]([CH3:2])=[C:4]2[C:8]=1[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 2200944,7-Dimethyl-1-indanone

Product 1

HCID 231514,7-DimethylindanYield 81.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent3×

Procedure

Zinc amalgam (prepared by mixing zinc dust (25.0 g), mercuric chloride (2.5 g), concentrated hydrochloric acid (3 ml) and water (50 ml) together for 5 minutes, then decanting the aqueous solution) was added to a mixture of 4,7-dimethylindan-1-one (25.0 g, 156 mmole), acetic acid (50 ml), water (50 ml) and concentrated hydrochloric acid (100 ml). The mixture was refluxed with vigorous stirring for 12 hours, then cooled, poured into water and extracted with diethyl ether. The ether extract was washed successively with water, dilute aqueous sodium bicarbonate solution and water. Then dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography over silica gel (eluant hexane) gave 4,7-dimethylindane (18.5 g, 81.4%) as an oil.

Workup

  1. customdecanting the aqueous solution)
  2. temperatureThe mixture was refluxed
  3. temperaturecooled
  4. extractionextracted with diethyl ether
  5. extractionThe ether extract
  6. washwas washed successively with water, dilute aqueous sodium bicarbonate solution and water
  7. dry with materialThen dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customPurification by column chromatography over silica gel (eluant hexane)

Sources & evidence

ORD record
ord-5593b5aa9ac94a8eb782b922c44b7df0
Source dataset
uspto-grants-1992_05
Patent number
US05110989

Reaction notes

Loading…