Dichloromethane → HCID 20080369, compound

HRID 1653657Notes

Reaction equation

HRID 1653657 reaction equation
[CH:1]([CH:4]1[C:12]2[C:7](=[CH:8][C:9](C)=[C:10]([CH3:13])[CH:11]=2)[C:6]([CH3:16])([CH3:15])[CH:5]1[CH3:17])([CH3:3])[CH3:2].C[O:19][CH:20](Cl)Cl.[CH2:23](Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH:20]([C:9]1[C:8]([CH3:23])=[C:7]2[C:12](=[CH:11][C:10]=1[CH3:13])[CH:4]([CH:1]([CH3:2])[CH3:3])[CH:5]([CH3:17])[C:6]2([CH3:16])[CH3:15])=[O:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 21004Methane, dichloromethoxy-HCID 20080383HCID 20080383, compound

Product 1

HCID 20080369HCID 20080369, compound

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

The compound 1-isopropyl-2,3,3,4,6-pentamethylindane is then treated as follows to yield 5-formyl-1-isopropyl-2,3,3,4,6-pentamethylindane. Specifically, 1-isopropyl-2,3,3,5,6-pentamethylindane (12.96 g) is placed in a 1 liter three-necked round bottom flask equipped with a reflux condenser, a stirrer and a dropping funnel. In accordance with the general procedures described in Organic Syntheses, Collective Vol. 5, pp. 49-50, by A. Rieche, H. Gross, and E. Hoft, edited by H. E. Baumgarten, John Wiley and Sons (New York, N.Y. 1973), methylene chloride (37.5 ml) is added to the flask. The solution is then cooled in an ice bath, and titanium tetrachloride (19.0 g) is added over a period of about 3 minutes. While the solution is stirred and cooled, α,α-dichloromethyl methyl ether (5.75 g) is added dropwise over a 25 minute period. After the addition is complete, the mixture is stirred for about 5 minutes in the ice bath, for about 30 minutes without cooling, and for about 15 minutes at about 35° C. The reaction mixture is then poured into a separatory funnel containing about 50 g of crushed ice and is shaken thoroughly. The organic layer is separated, and the aqueous solution is extracted with two 10 ml portions of methylene chloride. The combined organic solution is washed three times with 10 ml portions of water. A crystal of hydroquinone is added to the methylene chloride solution, which is then dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue is distilled to yield, as a crude product, 5-formyl-1-isopropyl-2,3,3,4,6-pentamethylindane. The 5-formyl-1-isopropyl-2,3,3,4,6-pentamethylindane is then further purified using standard fractional distillation techniques.

Workup

  1. customequipped with a reflux condenser, a stirrer and a dropping funnel
  2. temperatureThe solution is then cooled in an ice bath
  3. temperaturecooled
  4. additionAfter the addition
  5. temperaturewithout cooling
  6. additionThe reaction mixture is then poured into a separatory funnel
  7. stirringis shaken thoroughly
  8. customThe organic layer is separated
  9. extractionthe aqueous solution is extracted with two 10 ml portions of methylene chloride
  10. washThe combined organic solution is washed three times with 10 ml portions of water
  11. additionA crystal of hydroquinone is added to the methylene chloride solution, which
  12. dry with materialis then dried over anhydrous sodium sulfate
  13. customAfter evaporation of the solvent
  14. distillationthe residue is distilled

Sources & evidence

ORD record
ord-e8f3c7dc729f4376a67ffaf312ca0c41
Source dataset
uspto-grants-1995_04
Patent number
US05403823

Reaction notes

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