Hydrochloric Acid → 3-ethoxy-3-cyclobutene-1,2-dione

HRID 372626Notes

Reaction equation

HRID 372626 reaction equation
C([O:3][C:4]1(OCC)[C:7](OCC)([O:8][CH2:9][CH3:10])[CH2:6][C:5]1=[O:14])C.Cl>>[CH2:9]([O:8][C:7]1[C:4](=[O:3])[C:5](=[O:14])[CH:6]=1)[CH3:10]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 203263262,2,3,3-Tetraethoxycyclobutan-1-one

Product 1

HCID 110946163-ethoxy-3-cyclobutene-1,2-dioneYield 30%

Procedure

##STR7## 45 g of 2,2,3,3-tetraethoxycyclobutanone are stirred vigorously at 50° C in 4 normal aqueous HCl until the starting material is no longer detectable. The reaction solution is then extracted for 20 hours continuously with diethyl ether and the organic extracts are dried over MgSO4 and concentrated. Precipitated crystals of 1-hydroxycyclobutene-3,4-dione are filtered off sharply and the liquid residue is distilled at 110° C/0.1 Torr to yield 6.65 g (=30% of theory) of the desired 1-ethoxycyclobutene-3,4-dione of the above structure.

Workup

  1. extractionThe reaction solution is then extracted for 20 hours continuously with diethyl ether
  2. dry with materialthe organic extracts are dried over MgSO4
  3. concentrationconcentrated
  4. customPrecipitated crystals of 1-hydroxycyclobutene-3,4-dione
  5. filtrationare filtered off sharply
  6. distillationthe liquid residue is distilled at 110° C/0.1 Torr

Sources & evidence

ORD record
ord-196e75bb90e24370bbfbc5dcc3c35dfa
Source dataset
uspto-grants-1978_05
Patent number
US04092146

Reaction notes

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