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

HRID 2258501
ノート
印刷プレビュー

反応式

HRID 2258501 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049
Pyridine
溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c3b72c3ef46546498f37c54a616ac24d
出典データセット
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05661166

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート