Hydrochloric Acid → HCID 11074170, compound

HRID 871185Notes

Reaction equation

HRID 871185 reaction equation
[C:1](Cl)(=[O:6])/[C:2](=[CH:4]/[CH3:5])/[CH3:3].[CH3:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1.Cl>C(=S)=S>[CH3:3][CH:2]1[CH:4]([CH3:5])[C:11]2[C:10](=[C:9]([CH3:8])[CH:14]=[CH:13][C:12]=2[CH3:15])[C:1]1=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7809P-XyleneHCID 5325503(2E)-2-Methyl-2-butenoyl chloride

Product 1

HCID 11074170HCID 11074170, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
-10 °C

Procedure

Under an argon atmosphere A1Cl3 (64 g, 0.48 mol) and CS2 (250 ml) were placed in a 1 liter three necked round bottomed flask fitted with a magnetic stirring apparatus, an addition funnel, an inner thermometer and a reflux condenser. A mixture of tigloyl chloride (33) (42 g, 0.35 mol) and p-xylene (42.8 ml, 0.35 mol) was added over a period of 1 h at −10° C. under vigorous stirring. After 2 h stirring at −10° C. the mixture was allowed to come to ambient temperature and was stirred at that temperature overnight. The brown reaction mixture was then refluxed for 3 h, after cooling to ambient temperature the reaction mixture was poured carefully onto a mixture of concentrated HCl (300 ml) and ice (500 g). Then the mixture was transferred into a separation funnel, the lower CS2 layer was separated and the aqueous layer extracted with diethyl ether (3×100 ml). The combined organic layers were dried over magnesium sulfate, filtered, and the solvents removed in a rotary evaporator to give a red brown liquid. This residue was rectified using a 35 cm Vigreux column to afford 2,3,4,7-tetramethyl-1-indanone (35) (34 g, 52%, 95-100° C., 1.5-1.2 mbar) as a pale yellow liquid. (35) was found to be a mixture of the two isomers of 2,3,4,7-tetramethyl-1-indanone (35a to 35b approximately 3:1). The 1H NMR spectrum was identical with the literature (S. Barlow, D. R. Cary, M. J. Drewitt, D. O'Hare, J. Chem. Soc. Dalton Trans. 1997 3867-3878).

Workup

  1. customfitted with a magnetic stirring apparatus, an addition funnel
  2. additionwas added over a period of 1 h at −10° C. under vigorous stirring
  3. customto come to ambient temperature
  4. stirringwas stirred at that temperature overnight
  5. temperatureThe brown reaction mixture was then refluxed for 3 h
  6. temperatureafter cooling to ambient temperature the reaction mixture
  7. customThen the mixture was transferred into a separation funnel
  8. customthe lower CS2 layer was separated
  9. extractionthe aqueous layer extracted with diethyl ether (3×100 ml)
  10. dry with materialThe combined organic layers were dried over magnesium sulfate
  11. filtrationfiltered
  12. customthe solvents removed in a rotary evaporator
  13. customto give a red brown liquid

Sources & evidence

ORD record
ord-363fd387ef904846b9eb54a4dfb2b848
Source dataset
uspto-grants-2015_03
Patent number
US08969624B2

Reaction notes

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