Hydrochloric Acid → 2,7-Bis(acryloyloxy)-9-methylfluorene

HRID 1943537ノート

反応式

HRID 1943537 の反応式
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([OH:20])=[CH:14][CH:15]=3)[CH:10]([CH3:21])[C:9]=2[CH:8]=1.C(N([CH2:27][CH3:28])CC)C.Cl.[OH-:30].[Na+].Cl[CH2:33]Cl>C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.O>[C:33]([O:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([O:20][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:14][CH:15]=3)[CH:10]([CH3:21])[C:9]=2[CH:8]=1)(=[O:30])[CH:27]=[CH2:28]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 219606279-methyl-9H-fluorene-2,7-diol

生成物 1

HCID 672843372,7-Bis(acryloyloxy)-9-methylfluorene

試薬・触媒・溶媒 2

HCID 314042,6-Di-tert-butyl-4-methylphenol触媒HCID 962Water溶媒2 回

実験手順

Acryloyl chloride (55.4 g, 612.1 mmol) was added dropwise to a mixture of dichloromethane (500 mL), 2,7-dihydroxy-9-methylfluorene (T-11) (50.0 g, 235.6 mmol), triethylamine (61.7 g, 609.7 mmol) and 2,6-di-tert-butyl-p-cresol (52.0 mg, 0.24 mmol) in an ice bath under an atmosphere of nitrogen, and then the mixture was warmed slowly to room temperature. The stirring was continued at room temperature for 16 hours, and the reaction mixture was poured into water. The organic layer was wished with 1M-hydrochloric acid, aqueous 1M-sodium hydroxide solution and water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: toluene), and then by recrystallization from a mixed solvent of dichloromethane and ethanol to give colorless crystals (34.2 g) of 2,7-bis(acryloyloxy)-9-methylfluorene (1-3-4).

後処理

  1. dry with materialAfter the organic layer had been dried over anhydrous magnesium sulfate
  2. distillationthe organic solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (eluent: toluene)
  4. customby recrystallization from a mixed solvent of dichloromethane and ethanol

出典と根拠

ORDレコード
ord-3cc25621b2f84187a5d806add8184e5f
出典データセット
uspto-grants-2013_03
特許番号
US08394468B2

反応ノート

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