Catechol → HCID 22756306, compound

HRID 1579846Notes

Reaction equation

HRID 1579846 reaction equation
[CH:1]#[C:2][CH:3](OS(C1C=CC(C)=CC=1)(=O)=O)[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>[CH:1]#[C:2][CH:3]([O:17][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[OH:19])[CH3:4]

Participants

6

Reactant 4

HCID 289CatecholHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 561098p-Toluenesulfonic acid 1-butyn-3-yl ester

Product 1

HCID 22756306HCID 22756306, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 247 parts of p-toluenesulphonic acid-1-butin- 3-yl ester in 200 parts by volume of acetone is dropped at 50°C into a suspension of 110 parts of pyrocatechol, 152 parts of anhydrous potassium carbonate and 166 parts of potassium iodide in 100 parts by volume of acetone. The mixture is refluxed for 2 days, then filtered and evaporated. The residue is taken up in 500 parts by volume of ether, washed with water and with 450 parts by volume of sodium hydroxide solution of 20 % strength. The alkaline extract, together with the partially precipitated sodium salt of the product, is acidified with semidilute hydrochloric acid while being cooled with ice. The product is obtained by extracting this solution with chloroform and evaporating the extract. For purification it is distilled under a high vacuum. Boiling point: 63° to 66°C under 0.07 mm Hg. The distillate crystallises; it melts at 52° to 54°C.

Workup

  1. temperatureThe mixture is refluxed for 2 days
  2. filtrationfiltered
  3. customevaporated
  4. washwashed with water and with 450 parts by volume of sodium hydroxide solution of 20 % strength
  5. extractionThe alkaline extract, together with the partially precipitated sodium salt of the product
  6. temperaturewhile being cooled with ice
  7. customThe product is obtained
  8. extractionby extracting this solution with chloroform
  9. customevaporating the extract
  10. customFor purification it
  11. distillationis distilled under a high vacuum

Sources & evidence

ORD record
ord-df46d95366274c37a7cc5ba8fa800130
Source dataset
uspto-grants-1976_01
Patent number
US03931408

Reaction notes

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