Sulfuric Acid → o-Phenoxybenzaldehyde

HRID 260989

反応式

HRID 260989 の反応式
C([Li])CCC.[C:6]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(C)[CH:21]=[O:22].OS(O)(=O)=O>CCOCC>[O:12]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[CH:21]=[O:22])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 7583Diphenyl EtherHCID 178418339Butyllithium

生成物 1

HCID 88060o-Phenoxybenzaldehyde収率 69%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

At room temperature, under an argon atmosphere, n-butyllithium (15.45 mL of a 2.5M solution in hexanes, 38.61 mmol) was added to a solution of diphenyl ether (5.0 g; 29.38 mmol) in 100 mL of ether, and the reaction mixture was gently refluxed for 4 hrs. After cooling to 0° C., N,N-dimethylformamide (22.73 mL; 0.293 mol) was added dropwise and the reaction was stirred for 15 min at 0° C. and 1.5 hr at room temperature. After adding 10% H2SO4 to pH 1, it was stirred for 15 min and extracted into ethyl acetate. Chromatography of the crude product (10% ethyl acetate/hexane) provided 4.0 g (69%) of the aldehyde, 1H NMR (CDCl3): δ 6.97 (d, 1H); 7.02-7.11 (m, 2H); 7.18-7.22 (m, 2H); 7.29 (t, 1H); 7.39 (t, 1H); 7.43 (t, 1H); 7.95 (t, 1H).

後処理

  1. temperaturethe reaction mixture was gently refluxed for 4 hrs
  2. stirringwas stirred for 15 min
  3. extractionextracted into ethyl acetate

出典と根拠

ORDレコード
ord-4184c0fd57c2442bbebeb34cf477e9e1
出典データセット
uspto-grants-1996_06
特許番号
US05530157

関連ノート

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