Methanol → 4-(3-Ethynylphenoxy)naphthalic anhydride

HRID 2083657ノート

反応式

HRID 2083657 の反応式
[CH3:1][OH:2].C(C1C=[C:7]([C:11]2[CH:16]=[C:15](S([O-])(=O)=O)[CH:14]=[CH:13][C:12]=2C)[CH:8]=CC=1)#C.[OH-:22].[K+].Br[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35]([O:37][C:38]([C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43](Br)=[CH:42][CH:41]=2)=[O:39])=[O:36])=[CH:27][CH:26]=1>CS(C)=O.C(Cl)Cl.C(OCC)C>[C:7]([C:11]1[CH:16]=[C:1]([CH:14]=[CH:13][CH:12]=1)[O:2][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35]([O:37][C:38]([C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43]([O:22][C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([C:7]#[CH:8])[CH:16]=3)=[CH:42][CH:41]=2)=[O:39])=[O:36])=[CH:27][CH:26]=1)#[CH:8]

参加物

8

反応物 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 227546443-Ethynylphenyl(p-toluenesulfonate)HCID 57234554HCID 57234554、化合物

生成物 1

HCID 867356404-(3-Ethynylphenoxy)naphthalic anhydride収率 50%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

To 100 ml of anhydrous methanol was added 20 g (0.073 mole) of 3-ethynylphenyl(p-toluenesulfonate) and 8.19 g (0.146 mole) of potassium hydroxide. The mixture was heated to reflux, under a nitrogen atmosphere and maintained at reflux for four hours. The methanol solvent was removed in vacuo at 40° C by means of a rotary evaporator, leaving a dry, white powder. The white powder was dissolved in 100 ml of dimethylsulfoxide (DMSO) and added dropwise to a DMSO solution containing 13.8 g (0.05 mole) of 4-bromonaphthalic anhydride at 90° C. The mixture was heated at 100° C, under a nitrogen atmosphere, for 12 hours. The reaction mixture was allowed to cool to room temperature and poured into diethylether to precipitate the inorganic salts which were removed by filtration. The diethylether/DMSO solvent was removed in vacuo at 90° C, by means of a rotary evaporator leaving a residual oil. The oil was dissolved in methylene chloride and filtered through a 2 inch × 6 inch dry column of silica gel while eluting the column with methylene chloride. The eluate was evaporated to dryness, yielding 7.8 g (50%) of 4-(3-ethynylphenoxy)naphthalic anhydride.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux, under a nitrogen atmosphere
  3. temperaturemaintained
  4. temperatureat reflux for four hours
  5. customThe methanol solvent was removed in vacuo at 40° C by means of a rotary evaporator
  6. customleaving a dry, white powder
  7. temperatureto cool to room temperature
  8. customto precipitate the inorganic salts which
  9. customwere removed by filtration
  10. customThe diethylether/DMSO solvent was removed in vacuo at 90° C, by means of a rotary evaporator
  11. customleaving a residual oil
  12. filtrationfiltered through a 2 inch × 6 inch
  13. customdry column of silica gel
  14. washwhile eluting the column with methylene chloride
  15. customThe eluate was evaporated to dryness

出典と根拠

ORDレコード
ord-1d9072257818415dac278acaa37107a1
出典データセット
uspto-grants-1978_04
特許番号
US04086248

反応ノート

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