Myristyl bromide → 3-Methoxy-4-(tetradecyloxy)benzeneacetic acid ethyl ester

HRID 247975

反応式

HRID 247975 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2]

参加物

5

反応物 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 108965Ethyl homovanillate

生成物 1

HCID 537662243-Methoxy-4-(tetradecyloxy)benzeneacetic acid ethyl ester収率 68.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 50 g of 3-methoxy-4-hydroxybenzeneacetic acid ethyl ester, 66.1 g of powdered potassium carbonate, 70.57 g of 1-bromotetradecane and 500 ml of acetone is heated at reflux temperature for 76 hours. The reaction is cooled, filtered and the filtrate concentrated in vacuo. The residue is dissolved in methylene chloride, washed with 2% sodium bicarbonate and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane) to give 66.6 g of the desired product as colorless crystals.

後処理

  1. temperatureis heated
  2. temperatureat reflux temperature for 76 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. dissolutionThe residue is dissolved in methylene chloride
  7. washwashed with 2% sodium bicarbonate and saturated sodium chloride
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-454aed79c992449d876e390cfa9bf4a5
出典データセット
uspto-grants-1993_05
特許番号
US05208247

関連ノート

読み込み中…