4-Toluenesulfonyl chloride → O-(p-toluenesulfonyl)-m-phenoxymandelonitrile

HRID 1759419

反応式

HRID 1759419 の反応式
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.[C-:27]#[N:28].[Na+]>C(O)C>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O:12][CH:11]([C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)[C:27]#[N:28])(=[O:24])=[O:23])=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8929Sodium CyanideHCID 382843-Phenoxybenzaldehyde

生成物 1

HCID 12945136O-(p-toluenesulfonyl)-m-phenoxymandelonitrile収率 50.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 3.96 g of m-phenoxybenzaldehyde and 3.97 g of p-toluenesulfonyl chloride was stirred under ice cooling, and 10 ml of an aqueous solution containing 1.47 g of sodium cyanide was added dropwise over 30 minutes. Then, 10 ml of ethanol was added, and the mixture was stirred for 30 minutes under ice cooling, and then at room temperature for 30 minutes. The mixture was extracted with 30 ml of methylene chloride three times. The extract was washed with 20 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Recrystallization of the residue from ethanol afforded 3.816 g of O-(p-toluenesulfonyl)-m-phenoxymandelonitrile. The mother liquor was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel; hexane and benzene) to afford 1.846 g of O-(p-toluenesulfonyl)-m-phenoxymandelonitrile. The total amount of the product was 5.662 g (yield 75%). The product was in the form of colorless crystals.

後処理

  1. additionwas added dropwise over 30 minutes
  2. stirringthe mixture was stirred for 30 minutes under ice cooling
  3. extractionThe mixture was extracted with 30 ml of methylene chloride three times
  4. washThe extract was washed with 20 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization of the residue from ethanol

出典と根拠

ORDレコード
ord-6f0ed9bd60d04364974838efcbae9a41
出典データセット
uspto-grants-1982_07
特許番号
US04340740

関連ノート

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