Carbon Dioxide → 3-Hydroxy-7-methoxy-3-methyl-phthalide

HRID 1729166

반응식

HRID 1729166 반응식
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:6]([O:8][C:9](=[O:10])[C:4]=12)=[O:7].[C:14](O)(=O)CC(O)=O.C(N(CC)CC)C.C(=O)=O>O>[OH:7][C:6]1([CH3:14])[C:5]2[C:4](=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][CH:11]=2)[C:9](=[O:10])[O:8]1

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 867Malonic AcidHCID 8471TriethylamineHCID 2911934-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

생성물 1

HCID 199274383-Hydroxy-7-methoxy-3-methyl-phthalide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
73 °C

실험 절차

5.4 g of 3-methoxy-phthalic acid anhydride [see A. V. R. Rao et al., Indian J. Chew. 20B, 248 ff. (1981)], 4.7 g of malonic acid and 9 ml of triethylamine are heated slowly. The suspension becomes stirrable at 55° C. and, from 68° C., moderately vigorous CO2 evolution occurs. The internal temperature is maintained at 73° C. until gas evolution ceases (about 1 hour) and the reaction mixture is then heated at reflux temperature (internal temperature 85° C.) for a further 4 hours. When it has cooled, the reaction mixture is treated with water and extracted with ethyl acetate. The aqueous phase is then adjusted to pH 1.7 and extracted three times with fresh ethyl acetate, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. Fractional crystallisation (ethyl acetate/n-hexane) yields 3-hydroxy-7-methoxy-3-methyl-phthalide, m.p. 156°-158° C.; IR spectrum (CHCl3): C=O 1772 cm-1.

후처리

  1. custombecomes stirrable at 55° C. and, from 68° C.
  2. temperaturethe reaction mixture is then heated
  3. temperatureat reflux temperature (internal temperature 85° C.) for a further 4 hours
  4. temperatureWhen it has cooled
  5. extractionextracted with ethyl acetate
  6. extractionextracted three times with fresh ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customFractional crystallisation (ethyl acetate/n-hexane)

출처 및 근거

ORD 기록
ord-ffe60877d1be4aec983195fadfb84c74
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05332717

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