Acetone → 3-(2-Quinolinylmethoxy)benzeneacetic acid

HRID 414847ノート

反応式

HRID 414847 の反応式
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C(O[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1)(=O)C.[C:24](=[O:27])([O-])[O-:25].[K+].[K+].[CH3:30]C(C)=O>[I-].[K+]>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][O:23][C:19]1[CH:18]=[C:17]([CH2:30][C:24]([OH:25])=[O:27])[CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 5055AcetylresorcinolHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinoline

生成物 1

HCID 1285433-(2-Quinolinylmethoxy)benzeneacetic acid

試薬・触媒・溶媒 1

HCID 4875Potassium Iodide触媒

実験手順

A mixture of 2-chloromethyl quinolin (2.3 g, 13.3 mmol), 3-hydroxyphenyl acetate (2.2 g, 13.3 mmol), excess powdered potassium carbonate (10 g) and a catalytic amount of potassium iodide (0.1 g) in dry acetone (150 ml) was refluxed overnight (18 hr.). The reaction mixture was filtered, and the filtrate was concentrated, taken up in ethyl acetate, and the organic extract was washed with a 5% NaOH solution and brine. After drying over MgSO4, all volatiles were removed from the organic extract, and the crude oil was chromatographed on silica gel (20% ethylacetate in hexanes) to obtain the methyl ester of the desired product (3.0 g).

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. extractionthe organic extract
  4. washwas washed with a 5% NaOH solution and brine
  5. dry with materialAfter drying over MgSO4
  6. customall volatiles were removed from the organic extract
  7. customthe crude oil was chromatographed on silica gel (20% ethylacetate in hexanes)

出典と根拠

ORDレコード
ord-19d90a457c5d4b94bcb767515013d16d
出典データセット
uspto-grants-1988_12
特許番号
US04794188

反応ノート

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