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Ethanol → 2,5-Di(thiophen-2-yl)terephthalic acid

HRID 1473806
ノート
印刷プレビュー

反応式

HRID 1473806 の反応式
[OH-].[Na+].C(O)C.C[O:7][C:8](=[O:29])[C:9]1[CH:18]=[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1>O>[S:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:17]1[CH:18]=[C:9]([C:8]([OH:29])=[O:7])[C:10]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[CH:11][C:12]=1[C:13]([OH:15])=[O:14]
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 702EthanolHCID 14798Sodium HydroxideHCID 1045411Dimethyl 2,5-di(thiophen-2-yl)terephthalate

生成物 1

HCID 584350232,5-Di(thiophen-2-yl)terephthalic acid収率 84.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
78 °C

実験手順

Sodium hydroxide (4.80 g, 120.0 mmol) is dissolved in water (30 cm3), then ethanol (250 cm3) and 2,5-dithien-2-ylterephthalic acid dimethyl ester (5.30 g, 14.8 mmol) are added. This mixture is heated at 78° C. overnight. The solvent is evaporated under reduced pressure to about half of original volume then water is added. The resultant mixture is neutralized with concentrated hydrochloric acid. The precipitate is collected by filtration and washed with water and ethanol, then dried in vacuo, to yield the product as an off-white solid (4.13 g, 84%). 1H NMR (300 MHz, DMSO-d6): δ(ppm) 13.46 (s, 2H, COOH), 7.72 (s, 2H, Ar—H), 7.70 (dd, J=5.1 and 1.1 Hz, 2H, Ar—H), 7.28 (dd, J=3.6 and 1.1 Hz, 2H, Ar—H), 7.17 (m, 2H, Ar—H); 13C NMR (75 MHz, DMSO-d6): δ(ppm) 168.7 (C═O), 139.7 (q), 134.5 (q), 131.4 (q), 130.2 (CH), 127.9 (CH), 127.5 (CH), 127.1 (CH).

後処理

  1. customThe solvent is evaporated under reduced pressure to about half of original volume
  2. additionwater is added
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water and ethanol
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-efbf3843160a414eae5d4ecbf033a4bb
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09017577B2

反応ノート

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