Hydrochloric Acid → Ethyl-12-(m-iodophenyl)-dodecanoate

HRID 1089341ノート

反応式

HRID 1089341 の反応式
Cl.[CH2:2]([O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](N)[CH:18]=1)[CH3:3].N([O-])=O.[Na+].[I:29]I>CCOCC.C(O)(=O)C>[CH2:2]([O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([I:29])[CH:18]=1)[CH3:3]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 14584161Ethyl-12-(m-aminophenyl)-dodecanoateHCID 23668193Sodium Nitrite

生成物 1

HCID 14584162Ethyl-12-(m-iodophenyl)-dodecanoate収率 56.8%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒

実験手順

Glacial acetic acid (4 ml) and concentrated HCl (2.5 ml) were added to a 50 ml Erlenmeyer flask containing ethyl-12-(m-aminophenyl)-dodecanoate (3.92 g, 12.28 mmol). The mixture was cooled in a NaCl/ice bath. A cold aqueous solution of NaNO2 (4 ml, 3.1 M) was added to the mixture. The reaction was stirred for 40 minutes before a cold aqueous solution of KI/I2 2.31/1.78 g, 7 ml) was added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. Ether was added to the reaction mixture. The ether layer was separated and extracted with H2O, 10% Na2S2O3, H2O, sat. NaHCO3, and brine. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a reddish oil. The crude product was purified by column chromatography (120 g silica gel, hexanes:ethyl acetate 20:1) to yield a clear oil, compound 6, ethyl-12-(m-iodophenyl)-dodecanoate (5.28 g, 56.8% yield).

後処理

  1. temperatureThe mixture was cooled in a NaCl/ice bath
  2. additionwas added
  3. customThe ether layer was separated
  4. extractionextracted with H2O, 10% Na2S2O3, H2O, sat. NaHCO3, and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customto give a reddish oil
  8. customThe crude product was purified by column chromatography (120 g silica gel, hexanes:ethyl acetate 20:1)

出典と根拠

ORDレコード
ord-6fa52a62b1184dd896e368814a50c7db
出典データセット
uspto-grants-1990_10
特許番号
US04965391

反応ノート

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