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Acetic Acid → 2-(3-Hydroxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

HRID 1727006
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HRID 1727006 반응식
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([O:19]C(OC)=O)[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[O-]CC.[Na+].CC(O)=O>CCO>[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([OH:19])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 690371532-(3-Methoxycarbonyloxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

생성물 1

HCID 690411092-(3-Hydroxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
5 °C

실험 절차

1.35 g (4.1 mmol) of 2-(3-methoxycarbonyloxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester was dissolved in 30 ml of EtOH and cooled down to 5° C.; while stirring, 1.66 ml=1.45 g (4.5 mmol) of a solution of sodium ethoxide (21% in EtOH) was added and the reaction mixture then warmed up to ambient temperature. After 1 hour, it was poured into crashed ice/MeCl2, the pH was adjusted to 5-6 with AcOH (1N) and the reaction mixture was subsequently extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of MeCl2/MeOH) to finally give 0.95 g of the title compound as light brown oil.

후처리

  1. temperaturethe reaction mixture then warmed up to ambient temperature
  2. additionit was poured
  3. extractionthe reaction mixture was subsequently extracted twice with MeCl2
  4. washthe organic phases were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (SiO2, gradient of MeCl2/MeOH) to finally give 0.95 g of the title compound as light brown oil

출처 및 근거

ORD 기록
ord-cca1b42930cd47b2836738145e6e8fe1
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07495001B2

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