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Myristyl bromide → 4-Methoxy-3-(tetradecyloxy)benzoic acid methyl ester

HRID 247950
ノート
印刷プレビュー

反応式

HRID 247950 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>[I-].[Na+].CC(=O)CC>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21])[CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

生成物 1

HCID 536393154-Methoxy-3-(tetradecyloxy)benzoic acid methyl ester収率 71%

試薬・触媒・溶媒 2

HCID 5238Sodium Iodide触媒HCID 6569
Methyl Ethyl Ketone
溶媒

実験手順

A mixture of 45 g of product from Example 40, 51.2 g of finely powdered potassium carbonate, 72 g of 1-bromotetradecane, 1.9 g of sodium iodide and 500 ml of 2-butanone is heated at reflux temperature for 18 hours under an atmosphere of argon. The reaction is cooled and filtered. The filtrate is concentrated in vacuo and the residue is dissolved in chloroform. The organic layer is washed with 1N sodium hydroxide and saturated sodium chloride, dried and concentrated in vacuo. The residue is recrystallized from hexane to give 66.4 g of the desired product as white crystals.

後処理

  1. temperatureis heated
  2. temperatureat reflux temperature for 18 hours under an atmosphere of argon
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutionthe residue is dissolved in chloroform
  7. washThe organic layer is washed with 1N sodium hydroxide and saturated sodium chloride
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue is recrystallized from hexane

出典と根拠

ORDレコード
ord-a08e7576ffcc42b8ba5150c6dd881dbe
出典データセット
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05208247

反応ノート

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