Formaldehyde → 2-Hydroxymethyl-2-phenylheptanenitrile

HRID 333433ノート

反応式

HRID 333433 の反応式
[H-].[Na+].[C:3]1([CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]=[O:18]>CN(C=O)C>[OH:18][CH2:17][C:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:10]#[N:11]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 126520202-Phenylheptanenitrile

生成物 1

HCID 669878522-Hydroxymethyl-2-phenylheptanenitrile収率 71%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 1.34 g of 60% NaH in 50 mL of DMF cooled to 0° C. are added 5.14 g (27.4 mmol) of 2-phenylheptanenitrile. After stirring for 30 minutes, 7.6 g (220 mmol) of paraformaldehyde are added portionwise. The reaction medium is stirred at room temperature for 6 hours and then hydrolysed with ice and extracted with diethyl ether. The organic phase is washed with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate, filtered and evaporated under pressure. The crude product obtained is chromatographed on silica gel (eluent: 8/2 heptane/ethyl acetate). 4.24 g in the form of a pale yellow oil are obtained in a yield of 71%.

後処理

  1. stirringThe reaction medium is stirred at room temperature for 6 hours
  2. extractionhydrolysed with ice and extracted with diethyl ether
  3. washThe organic phase is washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under pressure

出典と根拠

ORDレコード
ord-de80ddab6c7340d38f93fa3ea3036a3e
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

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