Formaldehyde → 2-Hydroxymethyl-2-phenylheptanenitrile

HRID 540382ノート

反応式

HRID 540382 の反応式
[C:1]1([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:17]=[O:18]>CN(C=O)C>[OH:18][CH2:17][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:8]#[N:9]

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

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

後処理

  1. waitThe reaction medium is left
  2. stirringto stir at ambient temperature for 6 hours
  3. extractionhydrolysed with ice and extracted with diethyl ether
  4. washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under pressure

出典と根拠

ORDレコード
ord-16b9849e45e9416fa2bfd3498008499e
出典データセット
uspto-grants-2014_10
特許番号
US08871187B2

反応ノート

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