Acetonitrile → 3-(3-(Cyclooctylmethoxy)phenyl)-3-hydroxypropanenitrile

HRID 74382Notes

Reaction equation

HRID 74382 reaction equation
[CH:1]1([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH:14]=[O:15])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19](#[N:21])[CH3:20]>>[CH:1]1([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:14]([OH:15])[CH2:20][C:19]#[N:21])[CH:16]=[CH:17][CH:18]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 866376203-(Cyclooctylmethoxy)benzaldehyde

Product 1

HCID 673166323-(3-(Cyclooctylmethoxy)phenyl)-3-hydroxypropanenitrile

Procedure

Addition of acetonitrile to 3-(cyclooctylmethoxy)benzaldehyde gave 3-(3-(cyclooctylmethoxy)phenyl)-3-hydroxypropanenitrile as a yellow oil. Yield (0.90 g, 48%): 1H NMR (400 MHz, CDCl3) δ 7.25-7.31 (m, 1H), 6.91-6.95 (m, 2H), 6.84-6.89 (m, 1H), 5.01 (t, J=6.2 Hz, 1H), 3.72 (d, J=6.8 Hz, 2H), 2.74 (d, J=2.0 Hz, 2H), 1.97-2.04 (m, 1H), 1.33-1.79 (m, 14H).

Sources & evidence

ORD record
ord-fdd8046f1d6147b2bee28f21916f85fb
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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