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

HRID 247950
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HRID 247950 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 5238Sodium Iodide촉매HCID 6569
Methyl Ethyl Ketone
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a08e7576ffcc42b8ba5150c6dd881dbe
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05208247

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