Acetone → HCID 14766554, compound

HRID 1535005Notes

Reaction equation

HRID 1535005 reaction equation
CC(C)=O.[C:5]([OH:9])(=[O:8])[CH2:6][OH:7].[C:10](Cl)(=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>N1C=CC=CC=1>[C:10]([O:7][CH2:6][C:5]([OH:9])=[O:8])(=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 180Acetone2×HCID 757Glycolic AcidHCID 8124Octanoyl chloride

Product 1

HCID 14766554HCID 14766554, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

15.8 gm (0.20 mole) pyridine and 50 ml. acetone were combined in a 250 ml. round bottomed-three necked flask equipped with magnetic stir bar and two addition funnels, and cooled in an ice water bath with stirring. One addition funnel was charged with 15.5 gm (0.20 mole) glycolic acid dissolved in approximately 75 ml. acetone. The other addition funnel was charged with 32.5 gm (0.20 mole) octanoyl chloride. The contents of each addition funnel were added simultaneously to the cooled, stirred pyridine solution so that the complete addition of each component was continuous over one hour. The resultant slurry (a precipitation of pyridine hydrochloride was noted) was stirred an additional 45 minutes at ice bath temperature, and then at room temperature for another 30 minutes. Solvent was then removed by rotary evaporation at reduced pressure and 45C. The residual oil was dissolved in 200 ml dichloromethane and this was extracted with 3×150 ml. of 4% aqueous HCl. The dichloromethane layer was dried over sodium sulfate, decanted and the solvent removed by rotary evaporation. Drying on high vacuum for 4 hours left OOAA and 8.0% octanoic acid by weight, giving a crude yield for OOAA of 84%(mole). Recrystallization from 200 ml. hexane gave 27 g of a white crystalline product melting at 50 to 52° C., which was determined to be 99% wt. OOAA, giving a 67% (mole) yield of pure octanoxyloxyacetic acid.

Workup

  1. customround bottomed-three necked flask equipped with magnetic stir bar
  2. additiontwo addition funnels
  3. temperaturecooled in an ice water bath
  4. additionOne addition funnel
  5. dissolutiondissolved in approximately 75 ml
  6. additionThe contents of each addition funnel were added simultaneously to the cooled
  7. additionso that the complete addition of each component
  8. customThe resultant slurry (a precipitation of pyridine hydrochloride
  9. stirringwas stirred an additional 45 minutes at ice bath temperature
  10. waitat room temperature for another 30 minutes
  11. customSolvent was then removed by rotary evaporation at reduced pressure and 45C
  12. dissolutionThe residual oil was dissolved in 200 ml dichloromethane
  13. extractionthis was extracted with 3×150 ml
  14. dry with materialThe dichloromethane layer was dried over sodium sulfate
  15. customdecanted
  16. customthe solvent removed by rotary evaporation
  17. customDrying on high vacuum for 4 hours
  18. waitleft OOAA and 8.0% octanoic acid by weight
  19. customgiving a crude
  20. customyield for OOAA of 84%(mole)
  21. customRecrystallization from 200 ml

Sources & evidence

ORD record
ord-b56c7c128f034932aad7f95b33d75d9d
Source dataset
uspto-grants-1992_02
Patent number
US05091560

Reaction notes

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