Hydrochloric Acid → HCID 54084188, compound

HRID 871189Notes

Reaction equation

HRID 871189 reaction equation
[CH3:1][CH:2]1[CH:10]([CH3:11])[C:9]2[C:4](=[C:5]([CH3:13])[CH:6]=[CH:7][C:8]=2[CH3:12])[C:3]1=O.[CH3:15][Li].Cl.O>C(OCC)C>[CH3:15][CH:3]1[C:4]2[C:9](=[C:8]([CH3:12])[CH:7]=[CH:6][C:5]=2[CH3:13])[C:10]([CH3:11])=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11074170HCID 11074170, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 54084188HCID 54084188, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 1 liter three necked round bottomed flask fitted with a magnetic stirring apparatus and a reflux condenser 2,3,4,7-tetramethyl-1-indanone (35) (19.52 g, 0.1 mol) was dissolved in dry diethyl ether (300 ml) under an argon atmosphere. The mixture was cooled with ice and methyllithium (45 ml, 3 M solution in diethoxymethane, 0.135 mol) was added dropwise via a syringe, then the mixture was refluxed for 3 h. When the yellow reaction mixture had cooled a mixture of concentrated HCl (20 ml) and H2O (60 ml) was added via an addition funnel. The resulting mixture was transferred to a separation funnel and extracted with diethyl ether (3×200 ml). The combined organic layers were stirred overnight with 15 ml concentrated HCl. After this time the reaction mixture was carefully adjusted to pH 7 with a saturated aqueous solution of sodium carbonate. The reaction mixture was transferred into a separation funnel. The organic layer was washed with H2O (3×100 ml), dried over MgSO4, filtered and the solvent removed under reduced pressure to give a yellow liquid. This residue was purified via column-chromatography [(SiO2, 25×9 cm) eluent: cyclohexane] to afford 1,2,3,4,7-pentamethylindene (38) (8.35 g, 44%) as a yellow liquid; then (35) (starting material) (9.60 g, 49%) (eluent: cyclohexane:ethylacetate (10:1)) as a yellow liquid.

Workup

  1. additionwas added dropwise via a syringe
  2. temperaturethe mixture was refluxed for 3 h
  3. temperatureWhen the yellow reaction mixture had cooled
  4. additionwas added via an addition funnel
  5. customThe resulting mixture was transferred to a separation funnel
  6. extractionextracted with diethyl ether (3×200 ml)
  7. customThe reaction mixture was transferred into a separation funnel
  8. washThe organic layer was washed with H2O (3×100 ml)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure
  12. customto give a yellow liquid
  13. customThis residue was purified via column-chromatography [(SiO2, 25×9 cm) eluent: cyclohexane]

Sources & evidence

ORD record
ord-f13ad7b066874a778fc5d4764f57102e
Source dataset
uspto-grants-2015_03
Patent number
US08969624B2

Reaction notes

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