Phthalaldehydic acid → (3-Oxo-1,3-dihydro-isobenzofuran-1-yl)-phenyl-phosphinic acid

HRID 2090118Notes

Reaction equation

HRID 2090118 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.[C:12]1([PH:18](=[O:20])[OH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[O:3]=[C:1]1[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([P:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:19])[OH:20])[O:7]1

Participants

4

Reactant 2

HCID 8406Phthalaldehydic acidHCID 178527038HCID 178527038, compound

Product 1

HCID 57909088(3-Oxo-1,3-dihydro-isobenzofuran-1-yl)-phenyl-phosphinic acidYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

into a suspension of 30.1 grams (0.2 moles) of 2-carboxybenzaldehyde in 240 mL of toluene is added 28.4 grams (0.2 moles) of phenylphosphinic acid. The resultant mixture is heated to reflux and 3.8 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. The crude solid is recrystallized from 240 mL of methanol to give 31.8 grams (58% yield) of (3-oxo-1,3-dihydro-isobenzofuran-1-yl)-phenyl-phosphinic acid as white crystals, mp 230-233° C.

Workup

  1. temperatureto reflux
  2. distillation3.8 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
  6. customThe crude solid is recrystallized from 240 mL of methanol

Sources & evidence

ORD record
ord-fae6fdee2b444396a7f99509f2d3f462
Source dataset
uspto-grants-2013_05
Patent number
US08436131B2

Reaction notes

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