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Phthalic Anhydride → 5-(2-Carboxybenzoyloxy)-4-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one

HRID 2258501
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인쇄 미리보기

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HRID 2258501 반응식
[OH:1][CH:2]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6](=[O:11])[C:5]([CH3:12])=[CH:4][CH:3]1[O:13][CH3:14].[C:15]1(=[O:25])[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.CC1C=CN=C(N)C=1C.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[C:15]([O:1][CH:2]1[C:8]([CH3:9])([CH3:10])[CH2:7][C:6](=[O:11])[C:5]([CH3:12])=[CH:4][CH:3]1[O:13][CH3:14])=[O:25])([OH:20])=[O:19]
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참가 물질

6

반응물 4

HCID 6811Phthalic AnhydrideHCID 11430Potassium CarbonateHCID 110078842-Amino-3,4-dimethylpyridineHCID 229223715-Hydroxy-4-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one

생성물 1

HCID 229224315-(2-Carboxybenzoyloxy)-4-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one수율 53%

시약·촉매·용매 1

HCID 1049
Pyridine
용매

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온도
90 °C

실험 절차

To a solution of 5-hydroxy-4-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one (AU154) obtained in Example 4 (1.98 g, 10 mM) in pyridine (10 ml), phthalic anhydride (1.78 g, 12 mM) and dimethyl aminopyridine (0.05 g) were added and warmed to 90° C. for three hours, left to cool, poured onto ice-water, alkalified with potassium carbonate and extracted with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was crystallized from a mixed solvent of ethyl acetate and hexane to obtain 1.80 g (53%) of 5-(2-carboxybenzoyloxy)-4-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one (AU218) as colorless plates. Melting point: 158.0° to 158.5° C.

후처리

  1. additionwere added
  2. waitleft
  3. temperatureto cool
  4. additionpoured onto ice-water
  5. extractionextracted with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was crystallized from a mixed solvent of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-c3b72c3ef46546498f37c54a616ac24d
출처 데이터셋
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05661166

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