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Hydrogen Peroxide → 2-(5-Bromo-2-ethylphenyl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one

HRID 1193211
ノート
印刷プレビュー

反応式

HRID 1193211 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:19][CH3:20])=[C:6]([CH:18]=1)[CH:7]=[C:8]1[C:12]([CH3:14])([CH3:13])[O:11][C:10]([CH3:16])([CH3:15])[C:9]1=[O:17].[OH:21]O.[OH-].[Li+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:19][CH3:20])=[C:6]([CH:7]2[C:8]3([C:9](=[O:17])[C:10]([CH3:15])([CH3:16])[O:11][C:12]3([CH3:13])[CH3:14])[O:21]2)[CH:18]=1
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

5

反応物 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 668231984-(5-Bromo-2-ethylbenzylidene)-2,2,5,5-tetramethyldihydrofuran-3-one

生成物 1

HCID 866636592-(5-Bromo-2-ethylphenyl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one収率 87.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
35 °C

実験手順

To a solution of 4-(5-bromo-2-ethylbenzylidene)-2,2,5,5-tetramethyldihydrofuran-3-one (32.07 g, 95.15 mmol) in methanol (1570 ml) at 35° C. is added 50% aqueous hydrogen peroxide (8.10 ml, 142.73 mmol), followed immediately by a solution of 2M aqueous lithium hydroxide (9.51 ml, 19.03 mmol). This reaction mixture is stirred at 35° C. for exactly 1 hour, then quenched with saturated sodium metabisulfite (340 ml) and distilled water (340 ml). After stirring at room temperature for 15 minutes solvents are then concentrated in vacuo (to approximately 500 ml), over which time the product precipitates as a yellow solid. To this suspension is added distilled water (500 ml), and the product is isolated by filtration. After additional washing with distilled water the solid is dried under vacuum overnight to afford 2-(5-bromo-2-ethylphenyl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (29.30 g) as a yellow solid which is used without purification in the next step.

後処理

  1. customquenched with saturated sodium metabisulfite (340 ml)
  2. distillationdistilled water (340 ml)
  3. stirringAfter stirring at room temperature for 15 minutes solvents
  4. concentrationare then concentrated in vacuo (to approximately 500 ml), over which time the product
  5. customprecipitates as a yellow solid
  6. additionTo this suspension is added
  7. distillationdistilled water (500 ml)
  8. customthe product is isolated by filtration
  9. washAfter additional washing with distilled water the solid
  10. customis dried under vacuum overnight

出典と根拠

ORDレコード
ord-ac607ce88a714e5f823ba3b4175e6b62
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680299B2

反応ノート

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