Calcium Carbonate → Phthalaldehyde

HRID 1706051Notes

Reaction equation

HRID 1706051 reaction equation
Cl[CH:2](Cl)[C:3]1C(C(Cl)Cl)=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:13]([O-:16])(=O)[CH3:14].[Na+].C(=O)([O-])[O-:19].[Ca+2]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:7]1[CH:8]=[C:3]([CH:2]=[O:19])[C:14]([CH:13]=[O:16])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 1175761,2-Bis(dichloromethyl)benzeneHCID 517045Sodium Acetate

Product 1

HCID 4807PhthalaldehydeYield 72%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

In accordance with Example 1, a suspension consisting of 5.78 of α,α,α',α'-tetrachloroxylene (purity approx. 95%), 9.62 g of sodium acetate, 1.74 g of tetrabutylammonium bromide, 4.75 g of calcium carbonate and 10 ml of water is refluxed, with stirring, for 29 hours in a nitrogen atmosphere. After cooling, the reaction mixture is diluted with water and extracted with two 100 ml portions of ethyl acetate. The combined organic layers are washed with a saturated solution of sodium chloride and dried over magnesium sulfate. The solvent is distilled off in vacuo and the crystalline residue is dissolved in toluene and chromatographed through 100 g of silica gel. o-Phthalaldehyde is eluted with toluene/ethyl acetate (19:1) and the eluate is concentrated, affording 2.30 g (72%) of pure o-phthalaldehyde.

Workup

  1. temperatureis refluxed
  2. temperatureAfter cooling
  3. extractionextracted with two 100 ml portions of ethyl acetate
  4. washThe combined organic layers are washed with a saturated solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off in vacuo
  7. dissolutionthe crystalline residue is dissolved in toluene
  8. customchromatographed through 100 g of silica gel
  9. washo-Phthalaldehyde is eluted with toluene/ethyl acetate (19:1)
  10. concentrationthe eluate is concentrated

Sources & evidence

ORD record
ord-b5af04d0b67e457c8f7e57104a6597c7
Source dataset
uspto-grants-1980_06
Patent number
US04206152

Reaction notes

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