Catechol → HCID 131709893, compound

HRID 1579845Notes

Reaction equation

HRID 1579845 reaction equation
[CH2:1](OS(C1C=CC(C)=CC=1)(=O)=O)[C:2]#[C:3][CH3:4].[C:16]1([C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19])[OH:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:1]([O:17][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[OH:19])#[C:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 289CatecholHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 7018873But-2-yn-1-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 131709893HCID 131709893, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 122 parts of p-toluenesulphonic acid-2-butinyl ester in 150 parts by volume of acetone is dropped into a boiling mixture of 66 parts of pyrocatechol, 75 parts of potassium carbonate, 91 parts of potassium iodide and 360 parts by volume of acetone. The suspension is refluxed for 24 hours, then cooled, filtered and evaporated. The residue is taken up in ether, repeatedly washed with water and while being cooled with ice extracted with 200 parts by volume of sodium hydroxide solution of 10 % strength. The alkaline extract is neutralised with hydrochloric acid and the product taken up with chloroform. The solvent is evaporated and the product distilled at a bath temperature of 120°C under 0.05 mm Hg pressure. The distillate crystallises; it melts at 43° to 46°C.

Workup

  1. temperatureThe suspension is refluxed for 24 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated
  5. washrepeatedly washed with water
  6. temperaturewhile being cooled with ice
  7. extractionextracted with 200 parts by volume of sodium hydroxide solution of 10 % strength
  8. extractionThe alkaline extract
  9. customThe solvent is evaporated
  10. distillationthe product distilled at a bath temperature of 120°C under 0.05 mm Hg pressure

Sources & evidence

ORD record
ord-4508f3b4ee0f4980bdc27ab613f824ea
Source dataset
uspto-grants-1976_01
Patent number
US03931408

Reaction notes

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