Hydrochloric Acid → Ethyl 2-[4-(2-Hydroxyiminocyclohexan-1-ylmethyl)phenyl]propionate

HRID 971872Notes

Reaction equation

HRID 971872 reaction equation
[OH:1][N:2]=[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C([Li])CCC.I[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1.Cl>O1CCCC1.CCCCCC>[OH:1][N:2]=[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7517Cyclohexanone OximeHCID 21312279Ethyl 2-(4-iodomethylphenyl)propionateHCID 178418339Butyllithium

Product 1

HCID 73769774Ethyl 2-[4-(2-Hydroxyiminocyclohexan-1-ylmethyl)phenyl]propionateYield 11.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 3.95 g of hydroxyiminocyclohexane in 40 ml of tetrahydrofuran was added 45 ml of 15% n-hexane solution of n-butyllithium at room temperature. After the mixture was stirred for 30 minutes at the same temperature, a solution of 9.4 g of ethyl 2-(4-iodomethylphenyl)propionate in 30 ml of tetrahydrofuran was added and stirring was continued for further 1 hour at room temperature. The reaction mixture was poured into a mixture of 100 ml of ice-water and 20 ml of concentrated hydrochloric acid, and extracted with ether. The product thus obtained was purified through a chromatography on a column of silica gel [eluent: ethyl acetate -- methylene chloride (1:3)] to afford 1.0 g of the starting compound recovered and 4.5 g of the desired compound, which by recrystallization from a mixture of ether and n-hexane yielded colorless crystals, m.p. 102°-104° C.

Workup

  1. stirringstirring
  2. waitwas continued for further 1 hour at room temperature
  3. extractionextracted with ether
  4. customThe product thus obtained
  5. customwas purified through a chromatography on a column of silica gel [eluent: ethyl acetate -- methylene chloride (1:3)]

Sources & evidence

ORD record
ord-2d077ba3f0784b73b9c0622a621266f0
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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