Pyridine → HCID 70599963, compound

HRID 2163285Notes

Reaction equation

HRID 2163285 reaction equation
Cl[C:2](OCCCCCC1OC(=O)ON=1)=O.OCCCOC(=O)C(C)=C.N1C=CC=CC=1.[C:32]([O:37][CH2:38][CH:39]([C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]1[O:53][C:52](=[O:54])[O:51][N:50]=1)=[O:42])C)(=[O:36])[C:33]([CH3:35])=[CH2:34]>O1CCOCC1>[C:32]([O:37][CH:38]([CH3:2])[CH2:39][C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]1[O:53][C:52](=[O:54])[O:51][N:50]=1)=[O:42])(=[O:36])[C:33]([CH3:35])=[CH2:34]

Participants

6

Reactant 4

HCID 1049PyridineHCID 176943-Hydroxypropyl methacrylateHCID 22753193HCID 22753193, compoundHCID 70599985HCID 70599985, compound

Product 1

HCID 70599963HCID 70599963, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

In accordance with the procedure of Example 1, 35.34g (0.15 moles) 5-(chloroformyloxypentyl)-1,3,4-dioxazol-2-one is made to react with 21.63g (0.15 moles) hydroxypropylmethacrylate (a 1:1 mixture of 2-hydroxypropyl and 1-methyl-2-hydroxyethylmethacrylate) in 75 ml 1,4-dioxane by adding 11.86g (0.15 moles) pyridine in 65 ml 1,4-dioxane over a 1 hour period at 18-21° C. After work-up, 50.0g of a slightly reddish-brown liquid is obtained which is analyzed by IR and NMR spectroscopy to be a 1:1 mixture of 5-[(2-methacryloyloxy-1-methylethyl)formyloxypentyl]-1,3,4-dioxazol-2-one and 5-[(2-methacryloyloxy-2-methylethyl)formyloxypentyl]-1,3,4-dioxazol-2-one (yield: 97.2%), having the respective structural formulas: ##STR17##

Workup

  1. customAfter work-up, 50.0g of a slightly reddish-brown liquid is obtained which

Sources & evidence

ORD record
ord-75921e9d950c43b099be0ff9ef61f3ef
Source dataset
uspto-grants-1979_01
Patent number
US04133813

Reaction notes

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