Tetrahydrofuran → 2-Carbomethoxy-4-cyano-4-(o-chlorophenyl)cyclohexanone

HRID 1448544Notes

Reaction equation

HRID 1448544 reaction equation
CO[C:3](=[O:22])[CH2:4][CH2:5][C:6]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])([C:13]#[N:14])[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].ClC1C=CC(C(C#N)(CCC(O)=O)CCC(O)=O)=CC=1.O1CCCC1.CC(C)([O-])C.[K+]>C(O)(=O)C>[C:9]([CH:8]1[CH2:7][C:6]([C:13]#[N:14])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH2:5][CH2:4][C:3]1=[O:22])([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 12595520HCID 12595520, compoundHCID 204534054-(p-Chlorophenyl)-4-cyanopimelic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 125955292-Carbomethoxy-4-cyano-4-(o-chlorophenyl)cyclohexanoneYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part B, but substituting 39.11 gm. (0.121 mole) dimethyl-4-(o-chlorophenyl)-4-cyanopimelate (prepared in Part A, above) for the dimethyl ester of 4-(p-chlorophenyl)-4-cyanopimelic acid, and using 780 ml. of the tetrahydrofuran, 27.4 gm. (0.24 mole) of the potassium tert-butoxide, and 195 ml. of the 2.5 N acetic acid instead of the 700 ml., the 24.4 gm. (0.218 mole), and the 175 ml., respectively, there is prepared 33.4 gm. (95% yield) of 2-carbomethoxy-4-cyano-4-(o-chlorophenyl)cyclohexanone as a crystalline solid having a melting range of 113° to 118° C.

Workup

  1. custom, respectively, there is prepared 33.4 gm

Sources & evidence

ORD record
ord-a42900748aaf44da8783c4b51c068b29
Source dataset
uspto-grants-1979_12
Patent number
US04180584

Reaction notes

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