Acetic Acid → HCID 20453290, compound

HRID 462283Notes

Reaction equation

HRID 462283 reaction equation
C([CH:5]1[CH2:10][C:9]([C:19]#[N:20])([C:11]2[CH:16]=[CH:15][C:14](OC)=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:21])(OC)=O.[C:22](C1CC(C2C=CC(Cl)=CC=2)(C#N)CCC1=O)(OC)=[O:23].S(=O)(=O)(O)O.[C:47](O)(=O)C>>[C:19]([C:9]1([CH2:11][C:16]2[CH:15]=[CH:14][C:13]([O:23][CH3:22])=[CH:12][CH:47]=2)[CH2:10][CH2:5][C:6](=[O:21])[CH2:7][CH2:8]1)#[N:20]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanoneHCID 12230236HCID 12230236, compound

Product 1

HCID 20453290HCID 20453290, compoundYield 71%

Procedure

Following the procedure of Example 1, Part C, but substituting 41.5 gm. (0.145 mole) of 2-carbomethoxy-4-cyano-4-(p-methoxyphenyl)cyclohexanone [same as 2-carbomethoxy-4-cyano-4-(p-anisyl)cyclohexanone] (prepared in Part B, above) for the 29.8 gm. of 2-carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone, using 940 ml. glacial acetic acid and 470 ml. 10 percent aqueous sulfuric acid instead of the 660 ml. and 330 ml. respectively, and heating for 48 hours instead of 24 hours there is obtained 23.6 gm. (71% yield) of the expected 4-cyano-4-(p-anisyl)cyclohexanone which compound has a melting range at 84° to 86.5° C. An analytical sample recrystallized from diethyl ether has a melting range at 77.5° to 79.5° C.

Workup

  1. temperaturerespectively, and heating for 48 hours instead of 24 hours there
  2. customis obtained 23.6 gm

Sources & evidence

ORD record
ord-7fd8125102b1406c99c23636722a2050
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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