Catechol → HCID 12957960, compound

HRID 236216Notes

Reaction equation

HRID 236216 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-376ce1204bbb4fe98e2fc826b6e2e855
Source dataset
uspto-grants-1987_02
Patent number
US04642365

Reaction notes

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