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Sodium Hydroxide → HCID 13389168, 화합물

HRID 2164941
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HRID 2164941 반응식
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[C:25]([Cl:26])=[CH:24][C:23]([C:27](=[O:29])[CH3:28])=[C:22]([OH:30])[C:21]=2[CH2:31][CH2:32][CH3:33])[C:7]=1[CH2:34][CH2:35][CH3:36].[OH-].[Na+]>CO>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:37])=[O:2])=[C:7]([CH2:34][CH2:35][CH3:36])[C:8]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([C:27](=[O:29])[CH3:28])=[C:22]([OH:30])[C:21]=1[CH2:31][CH2:32][CH3:33])(=[O:14])[CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 14329994HCID 14329994, 화합물

생성물 1

HCID 13389168HCID 13389168, 화합물수율 42.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 1.94 g (0.0036 mol) of [4-acetyl-3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid methyl ester in 60 ml of methanol was added 60 ml of 1N sodium hydroxide (0.06 mol). The mixture was stirred at 25° for 20 hours. Most of the methanol was removed in vacuo and the aqueous solution was acidified to pH 4. The gummy precipitate was dissolved in ethyl acetate and washed with sodium chloride solution. The oil obtained on concentration of the ethyl acetate extract was purified by C18 reverse phase column chromatography, eluting with 60-80% methanol in water to yield a pale yellow oil which solidified. Recrystallization from cyclohexane-ether gave 790 mg, melting point 119°-121° (42% yield) of [4-acetyl-3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid.

후처리

  1. customMost of the methanol was removed in vacuo
  2. dissolutionThe gummy precipitate was dissolved in ethyl acetate
  3. washwashed with sodium chloride solution
  4. customThe oil obtained on concentration of the ethyl acetate
  5. extractionextract
  6. customwas purified by C18 reverse phase column chromatography
  7. washeluting with 60-80% methanol in water
  8. customto yield a pale yellow oil which
  9. customRecrystallization from cyclohexane-ether

출처 및 근거

ORD 기록
ord-324dd8e4da544c9cba13865c12fd595b
출처 데이터셋
uspto-grants-1985_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04507498

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