Oxalic Acid → HCID 20222015, compound

HRID 462888Notes

Reaction equation

HRID 462888 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:18])[CH2:10][CH2:11][CH:12]1OCCC[O:13]1.C(O)(=O)C(O)=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:18])[CH2:10][CH2:11][CH:12]=[O:13]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 20281493HCID 20281493, compound

Product 1

HCID 20222015HCID 20222015, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[3-(2,4-dichlorophenyl)but-3-en-1-yl]-1,3-dioxane (13.5 g) and oxalic acid (8.0 g) in water (100 ml) was heated in a flask fitted with a steam inlet and an anti-splash still head and condenser. The distillate, collected until almost no immiscible oily globules remained in the reaction flask, was extracted with diethyl ether. The extracts were washed with aqueous sodium bicarbonate and aqueous sodium chloride, the dried over magnesium sulphate and concentrated under reduced pressure to give 4-(2,4-dichlorophenyl)pent-4-enal (9.21 g, 86%), containing a trace of the reactant, as a pale yellow oil, 1H nmr (CDCl3): δ9.84 (1H, t J 2 Hz, CHO).

Workup

  1. temperaturewas heated in a flask
  2. customfitted with a steam inlet
  3. distillationThe distillate, collected until almost no immiscible oily globules
  4. extractionwas extracted with diethyl ether
  5. washThe extracts were washed with aqueous sodium bicarbonate and aqueous sodium chloride
  6. dry with materialthe dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c693c99418247a2be8cff975d64617c
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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