Phthalaldehydic acid → HCID 57909098, compound

HRID 2090115Notes

Reaction equation

HRID 2090115 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([OH:3])=O.[PH2:12]([OH:14])=[O:13]>C1(C)C=CC=CC=1>[O:7]=[C:6]1[C:5]2[C:4](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:1]([P:12]([CH:6]2[C:5]3[C:4](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:1](=[O:3])[O:7]2)(=[O:14])[OH:13])[O:3]1

Participants

4

Reactant 2

HCID 8406Phthalaldehydic acidHCID 4124402Phosphinic Acid

Product 1

HCID 57909098HCID 57909098, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a suspension of 30.1 grams (0.2 moles) of 2-carboxybenzaldehyde in 220 mL of toluene is added 10.4 mL (0.1 moles) of 50% aqueous hypophosphorous acid. The resultant mixture is heated to reflux and 9 mL of water is collected by azeotropic distillation using a Dean-Stark receiver. Upon cooling the reaction mixture, the precipitated white solid is collected by filtration and dried to give 30.2 grams (91% yield) of bis-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-phosphinic acid as a white powder, mp 280-285° C.

Workup

  1. temperatureto reflux
  2. distillation9 mL of water is collected by azeotropic distillation
  3. temperatureUpon cooling the reaction mixture
  4. filtrationthe precipitated white solid is collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-2d8995d501684d33ba6a26be398660a1
Source dataset
uspto-grants-2013_05
Patent number
US08436131B2

Reaction notes

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