Mandelonitrile → Cyano(phenyl)methyl 3,6-dichloro-2-methoxybenzoate

HRID 325253

反応式

HRID 325253 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([OH:10])[C:8]#[N:9])=[CH:3][CH:2]=1.N1C=C(C)C=C(C)C=1.[CH3:19][O:20][C:21]1[C:29]([Cl:30])=[CH:28][CH:27]=[C:26]([Cl:31])[C:22]=1[C:23](Cl)=[O:24]>C(Cl)Cl>[Cl:30][C:29]1[C:21]([O:20][CH3:19])=[C:22]([C:26]([Cl:31])=[CH:27][CH:28]=1)[C:23]([O:10][CH:7]([C:8]#[N:9])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:24]

参加物

5

反応物 3

HCID 10758MandelonitrileHCID 115653,5-DimethylpyridineHCID 82609Benzoyl chloride, 3,6-dichloro-2-methoxy-

生成物 1

HCID 13206467Cyano(phenyl)methyl 3,6-dichloro-2-methoxybenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

Benzaldehyde cyanohydrin (13.3 grams; 0.100 moles), 3,5-lutidine (11 grams) and methylene chloride (100 ml) were placed in a 500 ml. 3-necked glass reaction flask equipped with a mechanical stirrer, thermometer, condenser and addition funnel. This mixture was cooled to 10° C. by means of an ice bath and 2-methoxy-3,6-dichlorobenzoic acid chloride (23.9 grams; 0.10 moles) was added dropwise with the temperature of the mixture maintained at 5°-10° C. After the addition of the acid chloride was completed, the reaction mixture was stirred for an additional three hours at room temperature. After the reaction was completed, the mixture was washed three times with water, dried over anhydrous magnesium sulfate, filtered and concentrated by distillation. The residue was heated to a temperature of 150° C. under vacuum from a vacuum pump. Then the residue was dissolved in cyclohexane, treated with nuchar, filtered and stripped dry to give an oil.

後処理

  1. custom3-necked glass reaction flask
  2. customequipped with a mechanical stirrer
  3. additionthermometer, condenser and addition funnel
  4. temperaturemaintained at 5°-10° C
  5. washthe mixture was washed three times with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by distillation
  9. temperatureThe residue was heated to a temperature of 150° C. under vacuum from a vacuum pump
  10. dissolutionThen the residue was dissolved in cyclohexane
  11. additiontreated with nuchar
  12. filtrationfiltered
  13. customstripped dry
  14. customto give an oil

出典と根拠

ORDレコード
ord-9c4209d943364f8ca43ea4ab23b9381f
出典データセット
uspto-grants-1984_04
特許番号
US04440567

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