4-Benzoylbenzoic acid → Tri-n-butyl-(4-benzoyl-benzoyloxy)-tin

HRID 1881386Notes

Reaction equation

HRID 1881386 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([Sn:22]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])OC)[CH2:19][CH2:20][CH3:21]>ClCCCl>[CH2:29]([Sn:22]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:25][CH2:26][CH2:27][CH3:28])[O:14][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 691474-Benzoylbenzoic acidHCID 16683411Tributyltin methoxide

Product 1

HCID 68508746Tri-n-butyl-(4-benzoyl-benzoyloxy)-tinYield 41.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 50 ml dry three-neck-flask, 2.0 g (8.8 mmol) 4-benzoylbenzoic acid in 30 ml 1,2-dichlorethane are suspended under argon flow and heated to reflux. 2.8 g (8.8 mmol) tri-n-butylmethoxy tin are added slowly in the course of 0.5 h. The conversion is complete according to the 1H-NMR-spectrum. The slightly turbid hot solution is filtered, cooled and concentrated. 3.6 g of the crude product are obtained as yellowish oil. 2.4 g thereof are heated in a bulb-to-bulb distillation apparatus (0.03 mbar) and distilled at 190° C. 1.9 g of the title product is obtained as colorless oil. The structure is confirmed by 1H-NMR and 13C-NMR-spectra.

Workup

  1. customIn a 50 ml dry three-neck-flask
  2. temperatureheated to reflux
  3. filtrationThe slightly turbid hot solution is filtered
  4. temperaturecooled
  5. concentrationconcentrated
  6. custom3.6 g of the crude product are obtained as yellowish oil
  7. temperature2.4 g thereof are heated in a bulb-to-bulb distillation apparatus (0.03 mbar)
  8. distillationdistilled at 190° C

Sources & evidence

ORD record
ord-e127b5a293164734a91d62ff9df2e165
Source dataset
uspto-grants-2012_11
Patent number
US08318830B2

Reaction notes

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