Hydrochloric Acid → Tris(3,3-dimethylbutyl)tin chloride

HRID 66778Notes

Reaction equation

HRID 66778 reaction equation
CCCCC.C[Sn:7]([CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11].[ClH:26].O>C1C=CC=CC=1>[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][Sn:7]([Cl:26])([CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8003Pentane2×HCID 20529278Methyl tris(3,3-dimethylbutyl)tin

Product 1

HCID 86738521Tris(3,3-dimethylbutyl)tin chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tris(3,3-dimethylbutyl)tin chloride was prepared by the gradual addition of stannic chloride (13.0 g., 0.05 mole) dissolved in 50 c.c. pentane to a solution containing 19.5 g. (0.05 mole) of methyl tris(3,3-dimethylbutyl)tin dissovled in 50 c.c. pentane. The addition required 20 minutes and was performed under a nitrogen atmosphere. External cooling was applied as necessary to maintain the temperature of the reaction mixture below 27° C. Following completion of the addition the resulant mixture was heated at the boiling point for 0.5 hour, then allowed to cool to ambient temperature. A solution containing 2 c.c. of 12 normal aqueous hydrochloric acid and 100 c.c. water was added to the reaction mixture over a three minute period, followed by 50 c.c. of benzene. The organic liquid phase was separated, combined with 102 c.c. of an aqueous hydrochloric acid solution as previously described, after which the organic solvent was separated, dried using a portion of anhydrous magnesium sulfate and the organic solvents removed under reduced pressure. A 10 g. portion of the resultant white solid residue, obtained in 90% yield, was recrystallized from 100 c.c. of hexane and exhibited the following analysis, by weight:

Workup

  1. dissolutiondissolved in 50 c.c
  2. additionThe addition required 20 minutes
  3. temperatureExternal cooling
  4. temperatureto maintain the temperature of the reaction mixture below 27° C
  5. additioncompletion of the addition the resulant mixture
  6. temperaturewas heated at the boiling point for 0.5 hour
  7. additionA solution containing 2 c.c
  8. customThe organic liquid phase was separated
  9. customafter which the organic solvent was separated
  10. customdried
  11. customthe organic solvents removed under reduced pressure
  12. customportion of the resultant white solid residue, obtained in 90% yield
  13. customwas recrystallized from 100 c.c

Sources & evidence

ORD record
ord-f5d7d0c7c7ff456c970d8c82dc6dd990
Source dataset
uspto-grants-1982_08
Patent number
US04343815

Reaction notes

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