Acetic Acid → HCID 12888750, compound

HRID 1278021Notes

Reaction equation

HRID 1278021 reaction equation
C([O:4][CH2:5][CH:6]1[O:11][CH:10]([CH2:12][O:13][CH2:14][C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])[CH2:9][O:8][CH2:7]1)C=C.N1CCCCC1.[Mn]([O-])(=O)(=O)=O.[K+].Cl.S(=O)(O)[O-].[Na+].[C:42]([OH:45])(=[O:44])[CH3:43]>CC(C)=O.O.C(Cl)(Cl)Cl>[CH2:21]([N:17]([CH2:18][CH2:19][CH3:20])[C:15](=[O:16])[CH2:14][O:13][CH2:12][CH:10]1[O:11][CH:6]([CH2:5][O:4][CH2:43][C:42]([OH:45])=[O:44])[CH2:7][O:8][CH2:9]1)[CH2:22][CH3:23]

Participants

10

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 516875Potassium PermanganateHCID 23452408HCID 23452408, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 12888750HCID 12888750, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of 8.23 g (0.025 mole) of 2-[[6-[(2-propenyloxy)methyl]-1,4-dioxan-2-yl]methoxy]-N,N-dipropylacetamide in 350 ml of dry acetone is stirred at -20°, treated with 12.0 ml (0.12 mole) of piperidine and 9.53 g of potassium permanganate (0.06 mole). The mixture is stirred for 30 minutes, and treated below -20° with 2 ml of acetic acid in 25 ml of acetone. After 4 hours at -20°, 250 ml of chloroform is added (-20°), followed by careful addition of 30 ml of concentrated hydrochloric acid in 150 ml of water and 14 g of sodium bisulfite in 100 ml of water. Extraction with chloroform, evaporation and vacuum distillation of the resulting yellow oil, yields 4.3 g (54%), b.p. 131°-135° @ 0.1 mm, of the above compound.

Workup

  1. waitAfter 4 hours at -20°
  2. extractionExtraction
  3. customwith chloroform, evaporation and vacuum distillation of the resulting yellow oil
  4. customyields 4.3 g (54%), b.p. 131°-135° @ 0.1 mm

Sources & evidence

ORD record
ord-7d05cfafb6ab4735bebe834a9f42c46e
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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