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

HRID 1970104

반응식

HRID 1970104 반응식
[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>P(OP(O)(O)=O)(O)(O)=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]

참가 물질

6

반응물 4

HCID 962WaterHCID 1140TolueneHCID 8058HexaneHCID 66859650Methyl 2-(5-chloro-2-phenoxyphenyl)-3-hydroxyacrylate

생성물 1

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

시약·촉매·용매 1

HCID 1023Pyrophosphoric acid용매

반응 조건

온도
20 °C

실험 절차

A slurry of 2-(5-chloro-2-phenoxy-phenyl)-3-hydroxy-acrylic acid methyl ester (210 g, 691 mmol) was heated in pyrophosphoric 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).

후처리

  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

출처 및 근거

ORD 기록
ord-c2c2ea9c52f649e39657d96d689d23d4
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426610B2

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