5,6,7,8-Tetrahydro-2-naphthol → 1-Iodo-5,6,7,8-tetrahydro-2-naphthol

HRID 126956ノート

反応式

HRID 126956 の反応式
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].[I:12]Cl>C(O)(=O)C>[I:12][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].[I:12][C:3]1[C:2]([OH:11])=[CH:1][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1

参加物

5

反応物 2

HCID 143055,6,7,8-Tetrahydro-2-naphtholHCID 24640Iodine chloride

生成物 2

HCID 199116901-Iodo-5,6,7,8-tetrahydro-2-naphtholHCID 202877373-Iodo-5,6,7,8-tetrahydro-2-naphthol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A 4.45 g solution of 5,6,7,8-tetrahydro-2-naphthol was dissolved in 25 ml of glacial acetic acid, mixed with 5.85 g of iodine monochloride and heated under reflux at 100° C. for 2 hours. After reaction, the reaction mixture was poured onto 100 ml of ice water and extracted with ethyl acetate. The extract was washed sequentially with an aqueous solution of sodium thiosulfate (hypo), water and saturated aqueous NaCl solution, dried with anhydrous magnesium sulfate, and concentrated under vacuum. The residue was purified by column chromatography on silica gel using an eluting agent comprising a mixture (1:2) of methylene chloride and cyclohexane to provide white crystals each comprising 2.11 g of 1-iodo-5,6,7,8-tetrahydro-2-naphthol and 2.84 g of 3-iodo-5,6,7,8-tetrahydro-2-naphthol having the following physical properties.

後処理

  1. temperatureheated
  2. customAfter reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed sequentially with an aqueous solution of sodium thiosulfate (hypo), water and saturated aqueous NaCl solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography on silica gel using an eluting agent

出典と根拠

ORDレコード
ord-301da0f2579244539b68f36fb430317c
出典データセット
uspto-grants-1981_03
特許番号
US04254056

反応ノート

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