Dibutyltin oxide → HCID 59487992, compound

HRID 1881387Notes

Reaction equation

HRID 1881387 reaction equation
[CH2:1]([Sn:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[OH:11][C:12]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:21]O)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>C1(C)C=CC=CC=1>[CH2:1]([Sn:5]1([CH2:6][CH2:7][CH2:8][CH3:9])[O:11][C:12]([C:13](=[O:14])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][O:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 61221Dibutyltin oxideHCID 858062,3-Dihydroxy-1,2-diphenylpropan-1-one

Product 1

HCID 59487992HCID 59487992, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50 ml dry three-neck-flask 2.1 g (8.3 mmol) of dibutyltin oxide, 2.0 g (8.3 mmol) of 2,3-dihydroxy-1,2-diphenyl-propan-1-one [prepared according to H. J. Hageman, Macromolekulare Chemie, Rapid Communications (1981), 2(8), 517-521] and 20 ml of toluene are heated to reflux under argon flow. A small amount of water is distilled off the clear solution. According to the 1H-NMR-spectrum the conversion is complete after 2 h. The solution is concentrated and the crude product (4.0 g) is recrystallized from 15 ml of cyclohexane. The white crystals (2.3 g) are recrystallized from 10 ml of heptane and 3 ml of cyclohexane. 1.6 g of the title product is obtained as a white powder melting at 140-145° C. The structure is further confirmed by 1H-NMR and 13C-NMR-spectra.

Workup

  1. temperatureare heated
  2. temperatureto reflux under argon flow
  3. distillationA small amount of water is distilled off the clear solution
  4. concentrationThe solution is concentrated
  5. customthe crude product (4.0 g) is recrystallized from 15 ml of cyclohexane
  6. customThe white crystals (2.3 g) are recrystallized from 10 ml of heptane and 3 ml of cyclohexane

Sources & evidence

ORD record
ord-5cf62fc42ce24ef3b350987d64d9d44d
Source dataset
uspto-grants-2012_11
Patent number
US08318830B2

Reaction notes

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