Phthalaldehydic acid → HCID 57909098, compound

HRID 2381875Notes

Reaction equation

HRID 2381875 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-2896f9ef2c01461aac43a44b81f88d37
Source dataset
uspto-grants-2012_09
Patent number
US08258253B2

Reaction notes

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