Water → HCID 86584271, compound

HRID 481146Notes

Reaction equation

HRID 481146 reaction equation
[CH2:1]([Sn:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[OH2:11].[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[OH:11][CH2:18][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[OH:10].[CH2:1]([Sn:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 61221Dibutyltin oxide

Product 1

HCID 86584271HCID 86584271, compound

Procedure

The dibutyltin intermediate was prepared by a synthetic procedure reported in the literature. The diol 4 (80.4 g, 0.61 moles) was dissolved in 1 L toluene and transferred to a three-neck, 2-L flask fitted with a mechanical stirrer, thermometer, Dean Stark trap with extension adapter, and a reflux condenser. To the stirred reaction mixture was added 153.8 g 98% purity di-n-butyltin oxide, (Bu)2SnO. The mixture was then heated to reflux to azeotrope off the water of reaction. Initially, considerable foaming resulted and care was taken to prevent overflow into the Stark trap. The last traces of H2O were slowly removed at reflux (4 to 5 hr); total H2O collected: ˜11 mL. The mixture (a deep orange-brown color) was cooled to room temperature.

Workup

  1. customtransferred to a three-neck
  2. customTo the stirred reaction mixture
  3. temperatureThe mixture was then heated
  4. temperatureto reflux
  5. customInitially, considerable foaming resulted
  6. customThe last traces of H2O were slowly removed
  7. temperatureat reflux (4 to 5 hr)
  8. customtotal H2O collected

Sources & evidence

ORD record
ord-91bdf8a8cf774f16a58e968c6515b92e
Source dataset
uspto-grants-2003_11
Patent number
US06653486B2

Reaction notes

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