Catechol → HCID 86733239, compound

HRID 1605690Notes

Reaction equation

HRID 1605690 reaction equation
[OH-].[Na+].[C:3]1([C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)O)[OH:4].[CH3:11][O:12][C:13]1(C)C=CC(S([O-])(=O)=O)=C[CH:14]1[CH2:23]CC.CS(C)=[O:29]>O>[CH3:11][O:12][CH2:13][CH:14]([O:29][O:4][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:5]=1)[CH3:23]

Participants

6

Reactant 4

HCID 289CatecholHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 86733240HCID 86733240, compound

Product 1

HCID 86733239HCID 86733239, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

90 parts of 44.5% strength sodium hydroxide solution are added drop by drop under nitrogen to a solution of 110 parts of pyrocatechol and 244 parts of 1-methoxy-2-propyl-p-toluenesulphonate in 500 parts by volume of dimethylsulphoxide. During the addition, the temperature rises to 42°C. The mixture is stirred for 14 hours at room temperature, poured into 2000 parts of water, and extracted three times each time with 250 parts by volume of toluene. The toluene solution is washed twice each time with 200 parts of water, and evaporated. The residue is distilled in a high vacuum. Boiling point 70°-82°C/0.04 mm Hg.

Workup

  1. additionDuring the addition
  2. customrises to 42°C
  3. extractionextracted three times each time with 250 parts by volume of toluene
  4. washThe toluene solution is washed twice each time with 200 parts of water
  5. customevaporated
  6. distillationThe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-571200bfbd3d45eeacc5759e2e3309aa
Source dataset
uspto-grants-1976_04
Patent number
US03950533

Reaction notes

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