Pyridine → HCID 19909132, compound

HRID 1535007Notes

Reaction equation

HRID 1535007 reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].N1C=CC=CC=1.[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CC(C)=O>[C:18]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:2]([OH:3])[C:1]([OH:11])=[O:10])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 1292Mandelic AcidHCID 8124Octanoyl chloride

Product 1

HCID 19909132HCID 19909132, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

15.2 gm (0.10 mole) dl-mandelic acid was dissolved in 50 ml acetone and placed in one of two 125 ml additional funnels attached to a 250 ml three-necked round bottom flask charged with 8.0 gm (0.10 mole) pyridine in 50 ml acetone cooled in an ice water bath. The other addition funnel was charged with 16.3 gm (0.10 mole) octanoyl chloride. The contents of the two addition funnels were simultaneously added dropwise over 20 minutes to the stirred/cooled pyridine solution. The reaction was removed by rotary evaporation. The residue was dissolved in 200 ml diethyl ether and this solution was extracted with 5×150 ml 5% HCl, and then washed with 1×200 ml deionized water. The organic layer was dried over Na2SO4, filtered and the solvent removed by rotary evaporation. After drying in vacuo there remained 28.2 gm of oil. GC and 13C NMR determined this material to be 83.1% of the desired product, for an overall 84.2% yield.

Workup

  1. customattached to a 250 ml three-necked round bottom flask
  2. temperaturecooled in an ice water bath
  3. additionThe contents of the two addition funnels
  4. customThe reaction was removed by rotary evaporation
  5. dissolutionThe residue was dissolved in 200 ml diethyl ether
  6. extractionthis solution was extracted with 5×150 ml 5% HCl
  7. washwashed with 1×200 ml
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent removed by rotary evaporation
  11. dry with materialAfter drying in vacuo there remained 28.2 gm of oil

Sources & evidence

ORD record
ord-e162829529b54dda88ca1d0a54d85551
Source dataset
uspto-grants-1992_02
Patent number
US05091560

Reaction notes

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