6-Methoxy-3-(trichloromethyl)-2-benzofuran-1(3H)-one → Benzoic acid, 2-(2,2-dichloroethenyl)-5-methoxy-

HRID 2170125ノート

反応式

HRID 2170125 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]([C:13](Cl)([Cl:15])[Cl:14])[O:8][C:9]2=[O:12])=[CH:5][CH:4]=1>[Zn].C(O)(=O)C>[Cl:14][C:13]([Cl:15])=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:10]=1[C:9]([OH:12])=[O:8]

参加物

4

反応物 1

HCID 1578786-Methoxy-3-(trichloromethyl)-2-benzofuran-1(3H)-one

生成物 1

HCID 11543295Benzoic acid, 2-(2,2-dichloroethenyl)-5-methoxy-収率 64.4%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

A 100 mL round-bottomed flask containing a stirring bar was charged with 6-methoxy-3-(trichloromethyl)isobenzofuran-1(3H)-one (3.09 g, 10.94 mmol) and glacial acetic acid (40.0 mL). Zinc dust (2.86 g, 43.76 mmol) was added in small portions over 30 min. to the stirred reaction mixture. The reaction was left stirring at room temperature for further 30 min. and then heated at reflux for 1 h. It was filtered hot over a pad of Celite and the filtrates were diluted with water. The precipitate formed was collected by filtration and recrystallised from EtOH/H2O to give 2-(2,2-dichlorovinyl)-5-methoxybenzoic acid as white needles (1.74 g, 64%). Spectral data for this compound were consistent with those in the literature. M.p. 164-166° C. (lit. m.p. 167-168° C.); 1H NMR (400 MHz, DMSO-d6): δ=13.31 (br. s, 1H), 7.51 (d, J=8.7 Hz, 1H), 7.47-7.39 (m, 2H), 7.21 (dd, J=8.7 Hz, J=2.2 Hz, 1H), 3.82 (s, 3H).

後処理

  1. additionA 100 mL round-bottomed flask containing a stirring bar
  2. waitThe reaction was left
  3. temperatureheated
  4. temperatureat reflux for 1 h
  5. filtrationIt was filtered hot over a pad of Celite
  6. additionthe filtrates were diluted with water
  7. customThe precipitate formed
  8. filtrationwas collected by filtration
  9. customrecrystallised from EtOH/H2O

出典と根拠

ORDレコード
ord-d13c5a19b7eb4571b1b17d25dacde0e4
出典データセット
uspto-grants-2015_06
特許番号
US09050586B2

反応ノート

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