Phenylacetonitrile → HCID 10420427, compound

HRID 1108675Notes

Reaction equation

HRID 1108675 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]>>[OH:15][CH:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[N:9]

Participants

3

Reactant 2

HCID 8794PhenylacetonitrileHCID 12417Pivalaldehyde

Product 1

HCID 10420427HCID 10420427, compoundYield 87%

Procedure

Reaction of phenylacetonitrile and pivalaldehyde on a 30 mmol scale according to the procedure in Example 1, and recrystallization from toluene/hexane gave 5.34 g of the desired anti-aldol product (87%), m.p.: 70.7-71.2° C. NMR (1H, 13C), IR, and Mass spectra were consistent with the assigned structure. Analysis: Calculated for C13H17NO: C, 76.81; H, 8.42; N, 6.89. Found: C, 76.80; H, 8.43; N, 6.83.

Workup

  1. customaccording to the procedure in Example 1, and recrystallization from toluene/hexane

Sources & evidence

ORD record
ord-c15bf8a184d042dca273a13ff5772c34
Source dataset
uspto-grants-2000_05
Patent number
US06069177

Reaction notes

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