Toluene → Methyl 2-chlorodibenzo[b,f]oxepin-11-carboxylate

HRID 253747

反応式

HRID 253747 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:5]O.CCCCCC.C1(C)C=CC=CC=1>O>[CH3:1][O:2][C:3]([C:4]1[C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:5]=1)=[O:21]

参加物

5

反応物 3

HCID 1140TolueneHCID 8058HexaneHCID 66859650Methyl 2-(5-chloro-2-phenoxyphenyl)-3-hydroxyacrylate

生成物 1

HCID 58160327Methyl 2-chlorodibenzo[b,f]oxepin-11-carboxylate収率 86.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

A slurry of 2-(5-chloro-2-phenoxy-phenyl)-3-hydroxy-acrylic acid methyl ester (210 g, 691 mmol) was heated in pyrophosporic acid (420 g) to 60° C. After two hours, the reaction was cooled to 20° C. and hexane (250 mL), toluene (500 mL), and water (500 mL) were added to quench the reaction. The organic layer was separated and washed with saturated aqueous sodium bicarbonate (500 mL) and saturated brine (500 mL). The organic fraction was concentrated and the resulting oil was crystallized from n-butanol (500 mL; 20° C. for one hour and −10° C. for two hours), which provided the titled compound as off-white crystals (172 g, 85% yield for steps A and B). 1H NMR (400 MHz, CDCl3) 3.9 (s, 3H), 7.1-7.2 (m, 3H), 7.3 (m, 2H), 7.4 (t, 1H), 7.6 (d, 1H), 8.0 (s, 1H).

後処理

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate (500 mL) and saturated brine (500 mL)
  5. concentrationThe organic fraction was concentrated
  6. customthe resulting oil was crystallized from n-butanol (500 mL; 20° C. for one hour and −10° C. for two hours), which

出典と根拠

ORDレコード
ord-d9953e1b20404b6fae5269a6f44c5841
出典データセット
uspto-grants-2011_01
特許番号
US07872147B2

関連ノート

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