Pyridine → HCID 88789396, compound

HRID 2163283Notes

Reaction equation

HRID 2163283 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1O)[CH:2]=[CH2:3].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[O:30][C:29](=[O:31])[O:28][N:27]=1)=[O:19]>O1CCOCC1.C(Cl)(Cl)Cl>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:21]([O:20][CH:18]=[O:19])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[O:30][C:29](=[O:31])[O:28][N:27]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 156242-AllylphenolHCID 22753193HCID 22753193, compound

Product 1

HCID 88789396HCID 88789396, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent2×

Procedure

2-Allylphenol (4.70g = 0.035 moles) and 2.76g (0.035 moles) pyridine dissolved in 11 ml 1,4-dioxane are added over a 1 hour period to a well stirred solution of 8.25g (0.035 moles) 5-(chloroformyloxypentyl)-1,3,4-dioxazol-2-one in 25 ml 1,4-dioxane at 40° C. Stirring is continued at 53° C for 11/2 hours. The product is then dissolved in 150 ml chloroform, washed 3 times with ice water, dried over Drierite and evaporated under vacuum. The residue, 11.67g of yellow liquid is analyzed by IR and NMR spectroscopy and found to contain 69.4 wt. % of 5-[(o-allylphenyl)-formyloxypentyl]-1,3,4-dioxazol-2-one (yield = 69.4%), having the following structural formula: ##STR15##

Workup

  1. additionare added over a 1 hour period to a well
  2. customis continued at 53° C for 11
  3. custom2 hours
  4. washwashed 3 times with ice water
  5. dry with materialdried over Drierite
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-8914e0e4df28461e9af542552277b678
Source dataset
uspto-grants-1979_01
Patent number
US04133813

Reaction notes

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