Catechol → HCID 12957960, compound

HRID 2292387Notes

Reaction equation

HRID 2292387 reaction equation
[C:1]1([P:7](Cl)(Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[OH:14])[OH:12].C(N(CC)CC)C>CCOCC>[C:1]1([P:7]2(=[O:8])[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[O:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 8471TriethylamineHCID 69990Phenylphosphonic dichloride

Product 1

HCID 12957960HCID 12957960, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of 3.11 g of phenylphosphonic acid dichloride in 10 ml of ether were added 1.76 g of pyrocatechol and 20 ml of ether. The resulting solution was cooled to -25° C. to -28° C. and a solution of 3.23 g of triethylamine in 10 ml of ether was added dropwise thereto with stirring over 8 minutes. Thereafter, the reaction mixture was allowed to return to room temperature (20°-25° C.), and the precipitate was filtered off under nitrogen atmosphere and washed with 30 ml of ether. The filtrate and washings were combined and the ether was distilled off under reduced pressure to give 3.46 g (94.4% yield) of 2-phenyl-2-oxo-1,3,2-benzodioxaphosphole as a colorless oil. Upon standing in a refrigerator overnight, it crystallized.

Workup

  1. temperatureThe resulting solution was cooled to -25° C. to -28° C.
  2. customto return to room temperature
  3. custom(20°-25° C.)
  4. filtrationthe precipitate was filtered off under nitrogen atmosphere
  5. washwashed with 30 ml of ether
  6. distillationthe ether was distilled off under reduced pressure

Sources & evidence

ORD record
ord-49c8f63fd98f41d3b40df04dd7e524da
Source dataset
uspto-grants-1989_01
Patent number
US04801703

Reaction notes

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