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

HRID 247975

반응식

HRID 247975 반응식
[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]

참가 물질

5

반응물 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 108965Ethyl homovanillate

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-454aed79c992449d876e390cfa9bf4a5
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208247

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