Formaldehyde → 2-Hydroxymethyl-2-phenylheptanenitrile

HRID 333433Notes

Reaction equation

HRID 333433 reaction equation
[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]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 126520202-Phenylheptanenitrile

Product 1

HCID 669878522-Hydroxymethyl-2-phenylheptanenitrileYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-de80ddab6c7340d38f93fa3ea3036a3e
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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