2,4-Dihydroxybenzophenone → 2'-Hydroxy-4'-(pyridin-3-ylmethoxy)benzophenone

HRID 322965

反応式

HRID 322965 の反応式
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl.Cl[CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C.C(OCC)(=O)C.[I-].[K+]>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=[CH:12][C:3]=1[C:4](=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

8

反応物 3

HCID 85722,4-DihydroxybenzophenoneHCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochloride

生成物 1

HCID 220104602'-Hydroxy-4'-(pyridin-3-ylmethoxy)benzophenone収率 69.5%

試薬・触媒・溶媒 4

HCID 4875Potassium Iodide触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 6569Methyl Ethyl Ketone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2,4-dihydroxybenzophenone (21.4 g), 3-chloromethylpyridine hydrochloride (25 g), potassium carbonate (80 g), potassium iodide (0.5 g) and tetrabutylammonium bromide (0.2 g) in methyl ethyl ketone is heated at reflux with mechanical stirring for 18 hours. The reaction mixture is filtered through hyflo and the solids washed with several portions of methyl ethyl ketone. The filtrate and the washings are combined and concentrated under reduced pressure to leave a brown oil which is dissolved in ethyl acetate (250 mL) and washed four times with water (200 mL). The organic layer is dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a residue which is crystallised from cyclohexane containing a little decolourizing charcoal to give 2′-hydroxy-4′-(pyridin-3-ylmethoxy)benzophenone (21.2 g) as a pale yellow solid, m.p. 88-90° C.

後処理

  1. temperatureis heated
  2. temperatureat reflux
  3. filtrationThe reaction mixture is filtered through hyflo
  4. washthe solids washed with several portions of methyl ethyl ketone
  5. concentrationconcentrated under reduced pressure
  6. customto leave a brown oil which
  7. washwashed four times with water (200 mL)
  8. dry with materialThe organic layer is dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto leave a residue which
  12. customis crystallised from cyclohexane containing a little decolourizing charcoal

出典と根拠

ORDレコード
ord-90c536172a664ac392fc688c23ada996
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

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