Hydroquinone → Benzyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

反応式

[CH2:1]1[CH:5]2[C@@H:6]3C=C[C@H]([CH:4]2C=[CH:2]1)C3.[C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:14])[CH:12]=[CH2:13].C1(C=CC(O)=CC=1)O>>[CH2:16]([O:15][C:11]([CH:12]1[CH2:4][CH:5]2[CH2:6][CH:13]1[CH:2]=[CH:1]2)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

反応物 3

HCID 785Hydroquinone

HCID 75617Benzyl acrylate

HCID 15618652endo-Dicyclopentadiene

生成物 1

HCID 4083792Benzyl bicyclo[2.2.1]hept-5-ene-2-carboxylate収率 65%

反応条件

温度: 200 °C

実験手順

DCPD (dicyclopentadiene, Aldrich, 67.32 mL, 0.5 mol), benzyl acrylate (Lancaster, 163 g, 1.0 mol) and hydroquinone (0.23 g, 2.1 mmol) were charged into a 2 L high-pressure autoclave, and the temperature was raised to 200° C. The resulting mixture was reacted for 5 hours with stirring at 300 rpm. After the reaction was completed, the reaction mixture was cooled and transferred to a distilling apparatus. The reaction mixture was distilled twice under a reduced pressure (1 torr) using a vacuum pump to yield the title compound at 190° C. (yield: 65%, exo/endo=56/44).

後処理

customThe resulting mixture was reacted for 5 hours
temperaturethe reaction mixture was cooled
distillationThe reaction mixture was distilled twice under a reduced pressure (1 torr)

出典と根拠

ORDレコード: ord-d07cebf096ea4c038e0a5784a552dc19
出典データセット: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07718744B2

反応ノート

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