Acetic Acid → HCID 21411775, compound

HRID 2071657Notes

Reaction equation

HRID 2071657 reaction equation
OO.[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)(=[O:5])[CH3:4].C=O.[C:20]([OH:23])(=[O:22])[CH3:21]>>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]([O:23][C:20](=[O:22])[CH3:21])[CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:3](=[O:5])[CH3:4]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 784Hydrogen PeroxideHCID 21411755HCID 21411755, compound

Product 1

HCID 21411775HCID 21411775, compound

Conditions

Temperature
95 °C

Procedure

Aqueous hydrogen peroxide (13 mls of 30% solution) was added over 2 hours to a solution of 5-(2-pyridyl)-pentan-1-yl acetate (13.0 gms) in acetic acid (50 mls) at 75° C. After 16 hours and mixture was heated to 95° C and paraformaldehyde (1.8 gms) was added. After a further 2 hours the solvent was evaporated in vacuo and the residual oil was added to acetic anhydride (50 mls) and heated at 95° C for 6 hours. The solvent was evaporated and the product was poured onto ice, neutralised with potassium carbonate and extracted into diethyl ether. Evaporation of the ether and distillation of the residual oil yielded 1-(2-pyridyl)-1,5-diacetoxy pentane, b.p. 140°-141° C/1 mm (8 gms; 40%). Characterised by the following spectral data:

Workup

  1. customAfter a further 2 hours the solvent was evaporated in vacuo
  2. additionthe residual oil was added to acetic anhydride (50 mls)
  3. temperatureheated at 95° C for 6 hours
  4. customThe solvent was evaporated
  5. additionthe product was poured onto ice
  6. extractionextracted into diethyl ether
  7. customEvaporation of the ether and distillation of the residual oil

Sources & evidence

ORD record
ord-ba2c5cf69af142d4be1746a1a8c56ed9
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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