2-Ethyl-1-butanol → HCID 23025343, compound

HRID 1983813Notes

Reaction equation

HRID 1983813 reaction equation
[CH2:1]([Sn:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH2:11]([CH:13]([CH2:16][CH3:17])[CH2:14][OH:15])[CH3:12]>>[CH2:1]([Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([O:15][CH2:14][CH:13]([CH2:16][CH3:17])[CH2:11][CH3:12])[O:10][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:1][CH2:2][CH2:3][CH3:4])[O:15][CH2:14][CH:13]([CH2:16][CH3:17])[CH2:11][CH3:12])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 73582-Ethyl-1-butanolHCID 61221Dibutyltin oxide2×

Product 1

HCID 23025343HCID 23025343, compoundYield 99%

Procedure

A 500 ml recovery flask was charged with 59.8 g (0.15 mol) of dibutyltin oxide (manufactured by Aldrich Chemical Co., U.S.A., 98%) and 122 g (1.2 mol) of 2-ethyl-1-butanol (manufactured by Aldrich Chemical Co., U.S.A., 98%), whereby the flask contained the resulting white slurry mixture. The flask was attached to an evaporator (manufactured by Shibata Scientific Technology Ltd., Japan, R-144) connected to a thermoregulator-equipped oil bath (manufactured by Masuda Corporation, Japan, OBH-24), a vacuum pump (manufactured by ULVAC Inc., Japan, G-50A), and a vacuum controller (manufactured by Okano Works Ltd., Japan, VC-10S). The oil bath temperature was set at 140° C. The flask was immersed in the oil bath, whereupon rotation of the evaporator was started. Rotation was continued for about 30 minutes while stirring and heating under atmospheric pressure with the evaporator purge valve open. The evaporator purge valve was then closed, and the pressure in the system was gradually lowered to about 70 kPa using the vacuum pump and the vacuum controller. This state was maintained for 1 hour, after which the flask was removed from the oil bath. The reactant had turned a transparent liquid. The purge valve was gradually opened to return the system pressure to atmospheric pressure. The distillate was 3.6 g, transparent and had separated into 2 layers. Analysis of the distillate showed a water content of about 2.2 g. The flask was then removed from the oil bath and the purge valve was gradually opened to return the system pressure to atmospheric pressure. The flask yielded 175 g of reaction solution. Results of 119Sn, 1H and 13C-NMR analysis showed that, using dibutyltin oxide as a reference, the reaction solution contained about an 99% yield of 1,1,3,3-tetrabutyl-1,3-bis(2-ethyl-butyloxy)-distannoxane.

Workup

  1. customThe flask was attached to an evaporator (manufactured by Shibata Scientific Technology Ltd., Japan, R-144)
  2. customconnected to a thermoregulator-equipped oil bath
  3. customwas set at 140° C
  4. customThe flask was immersed in the oil bath, whereupon rotation of the evaporator
  5. temperatureheating under atmospheric pressure with the evaporator
  6. custompurge valve open
  7. customThe evaporator
  8. custompurge valve
  9. customwas then closed
  10. temperatureThis state was maintained for 1 hour
  11. customafter which the flask was removed from the oil bath
  12. customtransparent and had separated into 2 layers
  13. customThe flask was then removed from the oil bath
  14. customThe flask yielded
  15. custom175 g of reaction solution
  16. customResults of 119Sn, 1H and 13C-NMR analysis

Sources & evidence

ORD record
ord-ca4d1885dbbb4001893f5e1026da8f98
Source dataset
uspto-grants-2009_06
Patent number
US07541482B2

Reaction notes

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