Tetrahydrofuran → 2-Carbomethoxy-4-cyano-4-(p-tolyl)cyclohexanone

HRID 462287Notes

Reaction equation

HRID 462287 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)([CH2:9][CH2:10][C:11]([OH:13])=O)[CH2:4][CH2:5][C:6]([OH:8])=[O:7])#[N:2].Cl[C:22]1C=CC(C(C#N)(CCC(O)=O)CCC(O)=O)=CC=1.O1CCCC1.CC(C)([O-])C.[K+]>C(O)(=O)C>[C:6]([CH:5]1[CH2:4][C:3]([C:1]#[N:2])([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:9][CH2:10][C:11]1=[O:13])([O:8][CH3:22])=[O:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 204534054-(p-Chlorophenyl)-4-cyanopimelic acidHCID 20453466HCID 20453466, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 125955282-Carbomethoxy-4-cyano-4-(p-tolyl)cyclohexanoneYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part B, but substituting 42.44 gm. (0.14 mole) of the dimethyl ester of 4-cyano-4-(p-tolyl)pimelic acid (prepared in Part A, above) for the dimethyl ester of 4-(p-chlorophenyl)-4-cyanopimelic acid and using 900 ml. of the tetrahydrofuran, 31.5 gm. (0.28 mole) of the potassium tert-butoxide, and 225 ml. of the 2.5 N aqueous acetic acid instead of the 700 ml., the 24.4 gm. (0.218 mole), and the 175 ml., respectively, there is prepared 39.3 gm. (99% yield) of 2-carbomethoxy-4-cyano-4-(p-tolyl)cyclohexanone as a gum.

Workup

  1. custom, respectively, there is prepared 39.3 gm

Sources & evidence

ORD record
ord-f79690343f9246098274bda0f38766d8
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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