Oxalic Acid → 3-(2-Nitrophenoxy)propane-1,2-diol

HRID 262370Notes

Reaction equation

HRID 262370 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH:8]1[CH2:10][O:9]1)([O-:3])=[O:2].C(O)(=O)C(O)=[O:17].O1CCOCC1>O>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH:8]([OH:17])[CH2:10][OH:9])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 312751,4-DioxaneHCID 2199222-[(2-nitrophenoxy)methyl]oxirane

Product 1

HCID 202010383-(2-Nitrophenoxy)propane-1,2-diolYield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 38 parts of 2-(2-nitrophenoxymethyl)oxirane in 10 parts of ethanedioic acid and 300 parts of 1,4-dioxane are added 100 parts of water. The whole is stirred and refluxed for 2 days. The reaction mixture is evaporated and the residue is crystallized from a mixture of 2,2'-oxybispropane and petroleumether. The product is filtered off and recrystallized from 2,2'-oxybispropane, yielding 29.5 parts (13%) of 3-(2-nitrophenoxy)-1,2-propanediol; mp. 96° C.

Workup

  1. temperaturerefluxed for 2 days
  2. customThe reaction mixture is evaporated
  3. customthe residue is crystallized from a mixture of 2,2'-oxybispropane and petroleumether
  4. filtrationThe product is filtered off
  5. customrecrystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-92dd9a4726364006b4798fd66683463c
Source dataset
uspto-grants-1979_05
Patent number
US04154738

Reaction notes

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