Methyl vinyl ketone → HCID 14175218, compound

HRID 704291Notes

Reaction equation

HRID 704291 reaction equation
C(C1C=CC([OH:9])=CC=1F)#N.[CH3:11][C:12]1([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:17][CH2:16][CH:15](C2C=CC(C(Cl)=O)=CC=2)[CH2:14][CH2:13]1.[CH3:32][CH:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:34]=O.N1CCCC1.[CH:46]([C:48]([CH3:50])=[O:49])=[CH2:47]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:11][C:12]1([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:17][CH2:16][CH2:15][C:14](=[O:9])[CH2:13]1.[CH3:32][C:33]1([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:34][CH2:50][C:48](=[O:49])[CH2:46][CH2:47]1

Participants

9

Reactant 5

HCID 6570Methyl vinyl ketoneHCID 31268PyrrolidineHCID 860442-MethylheptanalHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 20075638HCID 20075638, compound

Product 2

HCID 14175218HCID 14175218, compoundHCID 20075879HCID 20075879, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A solution of 2.7 g of 4-cyano-3-fluorophenol and 5 ml of pyridine in 30 ml of toluene is added dropwise to a solution of 6.1 g of p-(4-methyl-4-n-pentylcyclohexyl)benzoyl chloride [obtainable by reaction of the enamine, obtainable from 2-methylheptanal and pyrrolidine, with methyl vinyl ketone according to G. Otani and S. Yamada, Chem. Pharm. Bull. 21(10), 2112-2118 (1973), hydrogenation of the resulting 4-methyl-4-pentyl-2-cyclohexanone to give 4-methyl-4-pentylcyclohexanone (an intermediate of the formula (A)), reaction With phenyl magnesium bromide, hydrolysis and hydrogenation to 4-methyl-4-n-pentylcyclohexylbenzene, reaction with acetyl chloride in the presence of aluminium chloride, subsequent haloform degradation of the resulting acetophenone to give the corresponding benzoic acid and conversion to the acid chloride] in 40 ml of toluene, and the mixture is boiled for 2 hours. After the customary working-up, 4-cyano-3-fluorophenyl p-(4-methyl-4-n-pentylcyclohexyl)benzoate is obtained.

Sources & evidence

ORD record
ord-41d1370de4404b908344bb3b7d3c22b1
Source dataset
uspto-grants-1991_01
Patent number
US04985583

Reaction notes

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