Water → Phthalaldehyde

HRID 1706050

반응식

HRID 1706050 반응식
Br[CH:2](Br)[C:3]1C(C(Br)Br)=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:13]([O-:16])(=O)[CH3:14].[Na+].C(=O)([O-])[O-:19].[Ca+2].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH:7]1[CH:8]=[C:3]([CH:2]=[O:19])[C:14]([CH:13]=[O:16])=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10112Calcium CarbonateHCID 832341,2-Bis(dibromomethyl)benzeneHCID 517045Sodium Acetate

생성물 1

HCID 4807Phthalaldehyde수율 66.2%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 8857Ethyl Acetate용매

실험 절차

With efficient stirring, a suspension consisting of 10 g (23.7 mmols) of α,α,α',α'-tetrabromo-o-xylene, 9.7 g (118 mmols) of sodium acetate. 1.74 g (5.4 mmols) of tetrabutylammonium bromide, 4.75 g of calcium carbonate and 10 ml of distilled water is heated to reflux in a nitrogen atmosphere, whereupon the temperature rises to 118° C. After a reaction time of 6 hours, the reaction mixture is cooled and, after the addition of 50 ml of ethyl acetate, filtered. The organic phase is separated in a separating funnel and the aqueous phase is washed once more with ethyl acetate. The combined organic extracts (ethyl acetate extracts) are washed with a solution of sodium chloride, dried over magnesium sulfate and then concentrated in vacuo. The residue is taken up in 40 ml of toluene and the solution is purified by chromatography through a column packed with 100 g of silica gel. After elution with toluene, concentration of the eluate yields 2.10 g (66.2% of theory) of o-phthalaldehyde with a melting point of 53°-55° C.

후처리

  1. temperatureto reflux in a nitrogen atmosphere, whereupon the temperature
  2. customrises to 118° C
  3. temperatureAfter a reaction time of 6 hours, the reaction mixture is cooled
  4. filtrationfiltered
  5. customThe organic phase is separated in a separating funnel
  6. washthe aqueous phase is washed once more with ethyl acetate
  7. washThe combined organic extracts (ethyl acetate extracts) are washed with a solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customthe solution is purified by chromatography through a column
  11. washAfter elution with toluene, concentration of the

출처 및 근거

ORD 기록
ord-96492b177b704c0e92dfccf1f0e727b1
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04206152

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