2-Methylbenzaldehyde → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 1789107Notes

Reaction equation

HRID 1789107 reaction equation
C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN=[C:21]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])(=O)=O)(C)C.[C:33]1(C)[C:34]([CH:39]=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=1>>[CH:34]1([CH:39]([OH:40])[C:21]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:22][CH2:23][N:24]([CH3:25])[CH3:26])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:33]1

Participants

3

Reactant 2

HCID 107222-MethylbenzaldehydeHCID 86741729beta-Dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone

Product 1

HCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-olYield 85.4%

Procedure

By using a method similar to that described in Example 22, but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and from o-tolualdehyde (5.78 g), 4-dimethylamino-1-(2-methylphenyl)-2-phenyl-2-buten-1-ol (Z) hydrochloride (10.2 g) is obtained in the form of a white powder melting at 204° C. after recrystallisation from ethanol (100 cc).

Sources & evidence

ORD record
ord-1119c717db4a4fe39ded8a3d3c1e6c12
Source dataset
uspto-grants-1987_08
Patent number
US04686309

Reaction notes

Loading…