HCID 13019168, compound → Chalcogran

HRID 1395675Notes

Reaction equation

HRID 1395675 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][C:4]#[C:5][CH2:6][CH:7]([OH:10])[CH2:8][CH3:9]>O.OS(O)(=O)=O.[Hg]=O>[CH2:8]([CH:7]1[CH2:6][CH2:5][C:4]2([CH2:3][CH2:2][CH2:1][O:11]2)[O:10]1)[CH3:9]

Participants

5

Reactant 1

HCID 13019168HCID 13019168, compound

Product 1

HCID 581383ChalcogranYield 76.7%

Reagents, catalysts & solvents 3

HCID 30856Mercuric oxideCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

0.540 g of mercury oxide in 100 ml of distilled water and 3.6 ml of concentrated H2SO4 were heated at 60° and at this temperature non-4-yn-1,7-diol (3.0 g) was added to the reaction mixture, which was then left 30 min under stirring. After cooling to room temperature, the mixture was extracted twice with diethyl ether washed with an aqueous solution of NaHCO3 and brine until neutrality, and finally dried over Na2SO4. The volatiles were taken off by evaporation in vacuo and the obtained residue was distilled in a bulb apparatus. 2.3 g (yield 35.2%) of the desired 2-ethyl-1,6-dioxaspiro[4.4]nonane having b.p. 80°-90°/1 Torr were thus obtained. The product had a purity of ca. 97%.

Workup

  1. additionwas added to the reaction mixture, which
  2. extractionthe mixture was extracted twice with diethyl ether
  3. washwashed with an aqueous solution of NaHCO3 and brine until neutrality
  4. dry with materialfinally dried over Na2SO4
  5. customThe volatiles were taken off by evaporation in vacuo
  6. distillationthe obtained residue was distilled in a bulb apparatus

Sources & evidence

ORD record
ord-2622f513c7ff4042809f195dbfc78d31
Source dataset
uspto-grants-1980_05
Patent number
US04205084

Reaction notes

Loading…