Oxalic Acid → 1-[2-(2,4-Dichlorophenyl)ethyl]ethanediol

HRID 1706892Notes

Reaction equation

HRID 1706892 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH:11]1[CH2:13][O:12]1.C(O)(=O)C(O)=[O:16].O1CCOCC1>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([OH:16])([OH:12])[CH3:13]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 312751,4-DioxaneHCID 198131652-[2-(2,4-Dichlorophenyl)ethyl]oxirane

Product 1

HCID 203326861-[2-(2,4-Dichlorophenyl)ethyl]ethanediol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 parts of [2-(2,4-dichlorophenyl)ethyl]-oxirane, 7 parts of ethanedioic acid, 300 parts of 1,4-dioxane and 150 parts of water is stirred and refluxed for 36 hours. The reaction mixture is evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried at the air, yielding 1-[2-(2,4-dichlorophenyl)ethyl]ethanediol; mp. 83.2° C.

Workup

  1. temperaturerefluxed for 36 hours
  2. customThe reaction mixture is evaporated
  3. customThe residue is crystallized from 2,2'-oxybispropane
  4. filtrationThe product is filtered off
  5. customdried at the air

Sources & evidence

ORD record
ord-6ccebad5c2014f2a982fa5e8ad842885
Source dataset
uspto-grants-1980_06
Patent number
US04209447

Reaction notes

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