Tributyltin Chloride → HCID 13019239, compound

HRID 596752Notes

Reaction equation

HRID 596752 reaction equation
[CH2:1]([Sn:5]([CH2:18][CH2:19][CH2:20][CH3:21])([CH:12]1CC[CH2:15][CH2:14][CH2:13]1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][CH3:4].[CH:22]1([Mg]Cl)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[CH2:30]([Sn:34]([Cl:43])(CCCC)[CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33].C([Sn](CCCC)(CCCC)C1CCCCC1)CCC>[Hg].CCCCC>[CH2:18]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:19][CH2:20][CH3:21].[CH2:30]([Sn:34]([Cl:43])([CH2:35][CH2:36][CH2:37][CH3:38])[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:31][CH2:32][CH3:33]

Participants

8

Reactant 4

HCID 15096Tributyltin ChlorideHCID 534724HCID 534724, compoundHCID 11101403HCID 11101403, compoundHCID 178478990HCID 178478990, compound

Product 2

HCID 534724HCID 534724, compoundHCID 13019239HCID 13019239, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 8003PentaneSolvent2×

Conditions

Temperature
36 °C

Procedure

Tributylcyclohexyl stannane was prepared using a procedure similar to that described in Example 1 for dibutyldicyclohexyl stannane, with the exception that a 25% molar excess of cyclohexylmagnesium chloride was reacted with tributyltin chloride. The boiling point of the product was 123° C. under a pressure of 0.7 mm. of mercury. A solution containing 37.3 grams (0.1 mole) of tributylcyclohexyl stannane in 50 cc. of pentane was placed in a reaction vessel equipped with a thermometer, mechanically driven stirrer, addition funnel, watercooled reflux condenser, and nitrogen inlet. To this was gradually added over a 25 minute period a solution containing 6.1 grams (0.1 mole) of stannic chloride in 50 cc. of pentane. During the addition, the temperature of the reaction mixture rose from 25° to 36° C. and the initially clear, colorless solution turned cloudy and yellow. After heating the solution to reflux temperature (36° C.) for 15 minutes, it was allowed to cool to ambient temperature. The product was extracted using 55 cc. of a 1.2 molar aqueous hydrochloric acid solution. The resultant two-phase mixture was transferred to a separatory funnel and the lower aqueous layer drawn off and discarded. The organic layer was extracted with two-50 cc. portions of 1.2 molar aqueous hydrochloric acid solution followed by two-50 cc. portions of water. The organic layer was then dried over anhydrous sodium sulfate, which was subsequently removed by filtration. The filtrate was concentrated using a rotary evaporator to yield 32.8 grams (93.2% yield) of dibutylcyclohexyltin chloride, a hazy, colorless liquid exhibiting an index of refraction (nD25) of 1.5079. The crude product was distilled under reduced pressure to yield 29.3 grams of dibutylcyclohexyltin chloride boiling between 139° and 140° C. at a pressure between 0.8 and 0.9 millimeter of mercury.

Workup

  1. customwas 123° C. under a pressure of 0.7 mm
  2. customequipped with a thermometer, mechanically driven stirrer, addition funnel
  3. temperaturewatercooled reflux condenser, and nitrogen inlet
  4. additionTo this was gradually added over a 25 minute period a solution
  5. additionDuring the addition
  6. customrose from 25° to 36° C.
  7. temperatureAfter heating the solution
  8. temperatureto cool to ambient temperature
  9. extractionThe product was extracted
  10. customThe resultant two-phase mixture was transferred to a separatory funnel
  11. extractionThe organic layer was extracted with two-50 cc
  12. dry with materialThe organic layer was then dried over anhydrous sodium sulfate, which
  13. customwas subsequently removed by filtration
  14. concentrationThe filtrate was concentrated
  15. customa rotary evaporator

Sources & evidence

ORD record
ord-d646bbc6b911400a8e8714579744737d
Source dataset
uspto-grants-1977_03
Patent number
US04012347

Reaction notes

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