Formaldehyde → 2-Hydroxymethyl-2-phenylheptanenitrile

HRID 540382Notes

Reaction equation

HRID 540382 reaction equation
[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]

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

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%.

Workup

  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

Sources & evidence

ORD record
ord-16b9849e45e9416fa2bfd3498008499e
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

Loading…