Cyclohexanecarboxaldehyde → HCID 44248498, compound

HRID 1108673Notes

Reaction equation

HRID 1108673 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[CH:12]1([CH:18]=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:12]1([CH:18]([OH:19])[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]#[N:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 16275CyclohexanecarboxaldehydeHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 44248498HCID 44248498, compoundYield 68%

Procedure

Reaction of p-methoxyphenylacetonitrile and cyclohexane-carboxaldehyde on a 20 mmol scale according to the procedure in Example 1, and two successive recrystallizations from chloroform/hexane gave 3.51 g of the desired anti-aldol product (68%), mp: 112.0-113.2° C. NMR (1H, 13C), IR, and Mass spectra were consistent with the assigned structure. Analysis: Calcd for C16H21NO2 : C, 74.10; H, 8.16; N, 5.40. Found: C, 74.25; H, 8.15; N, 5.39.

Workup

  1. customaccording to the procedure in Example 1, and two successive recrystallizations from chloroform/hexane

Sources & evidence

ORD record
ord-e2e6efd0d671460097368df0e18fbc86
Source dataset
uspto-grants-2000_05
Patent number
US06069177

Reaction notes

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