Phenylglyoxylic Acid → HCID 59487971, compound

HRID 1881390Notes

Reaction equation

HRID 1881390 reaction equation
[C:1]1([C:7](=[O:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:12].[Na+].[CH2:14]([Sn:18](Cl)(Cl)[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>O.C1COCC1>[C:1]1([C:7](=[O:11])[C:8]([O:9][Sn:18]([O:9][C:8](=[O:10])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:11])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11915Phenylglyoxylic AcidHCID 12688Dibutyltin dichlorideHCID 14798Sodium Hydroxide

Product 1

HCID 59487971HCID 59487971, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 50 ml dry three-neck-flask, 4.9 g (33.0 mmol) of phenylglyoxylic acid are dissolved under nitrogen in solution, of 1.45 g (36.3 mmol) of NaOH in 6 ml water at 0° C. 5.0 g (16.5 mmol) dibutyltin dichloride in 15 ml THF are added dropwise in the course of 0.5 h at 0° C. The emulsion is slowly warmed to room temperature, then heated to 40° C. and stirred for 30 min. The formed oil is separated off and the aqueous phase is extracted several times with methylene chloride. The oil and the methylene chloride phases are combined, dried over MgSO4, filtered and concentrated. The resulting oil is dissolved with heating in 20 ml of pentane and 10 ml of toluene and cooled. The crystals are filtered off at 0° C., dissolved in 20 ml of acetonitrile and extracted with 10 ml of heptane. The acetonitrile solution is concentrated affording 2.6 g of the title product as a yellow oil, which is recrystallized from 10 ml of pentane and 4 ml of ortho-xylene. The white crystals melt at 82-84° C. The structure of the product is further confirmed by 1H-NMR- and 13C-NMR-spectra.

Workup

  1. customIn a 50 ml dry three-neck-flask
  2. temperatureheated to 40° C.
  3. customThe formed oil is separated off
  4. extractionthe aqueous phase is extracted several times with methylene chloride
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe resulting oil is dissolved
  9. temperaturewith heating in 20 ml of pentane
  10. temperature10 ml of toluene and cooled
  11. filtrationThe crystals are filtered off at 0° C.
  12. dissolutiondissolved in 20 ml of acetonitrile
  13. extractionextracted with 10 ml of heptane
  14. concentrationThe acetonitrile solution is concentrated

Sources & evidence

ORD record
ord-516148dd7ca0425fb90a3c5e21f68aa4
Source dataset
uspto-grants-2012_11
Patent number
US08318830B2

Reaction notes

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