4-Hydroxybenzophenone → 4-[(Tributylstannyl)oxy]-benzophenone

HRID 1881384Notes

Reaction equation

HRID 1881384 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:16]([Sn:20]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])OC)[CH2:17][CH2:18][CH3:19]>ClCCCl>[CH2:27]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:23][CH2:24][CH2:25][CH3:26])[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 143474-HydroxybenzophenoneHCID 16683411Tributyltin methoxide

Product 1

HCID 685082484-[(Tributylstannyl)oxy]-benzophenoneYield 81%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

In a 50 ml dry three-neck-flask 1.5 g (7.6 mmol) of 4-hydroxy-benzophenone are suspended in 25 ml of 1,2-dichloroethane and heated to reflux under argon flow. 2.7 g (8.4 mmol) of tri-n-butylmethoxy tin are added to the solution in the course of 0.5 h. The conversion is complete according to the 1H-NMR-spectrum. The solution is concentrated and dried in high vacuum. 4.1 g of an orange oil crystallize. The crude product is dissolved at 90° C. in 20 ml of heptane. The solution is cooled and at about 60° C. brown crystals begin to form. After filtration, further cooling and freezing, the formation of crystals continues. The crystals are filtered, dried and analyzed. The structure is confirmed by 1H-NMR and 13C-NMR spectra. 3.0 g of the title product are obtained, melting at 76-82° C.

Workup

  1. temperatureheated
  2. temperatureto reflux under argon flow
  3. concentrationThe solution is concentrated
  4. customdried in high vacuum
  5. custom4.1 g of an orange oil crystallize
  6. dissolutionThe crude product is dissolved at 90° C. in 20 ml of heptane
  7. customto form
  8. filtrationAfter filtration
  9. temperaturefurther cooling
  10. filtrationThe crystals are filtered
  11. customdried

Sources & evidence

ORD record
ord-f8fde8a5c2084d9dab3b50dceb35a117
Source dataset
uspto-grants-2012_11
Patent number
US08318830B2

Reaction notes

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