Benzoyl chloride → HCID 15615679, compound

HRID 2165988Notes

Reaction equation

HRID 2165988 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:10]=[C:11]1[CH2:16][C:15](=[O:17])[CH2:14][CH:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12]1>ClCCl.C(N(CC)CC)C>[C:1]([O:17][C:15]1[CH2:14][CH:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][C:11](=[O:10])[CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 11252382Cyclohexanecarboxylic acid, 3,5-dioxo-, ethyl ester

Product 1

HCID 15615679HCID 15615679, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

7.75 g (55.1 mmol) Benzoyl chloride was added dropwise to 10.00 g (54.3 mmol) ethyl 3,5-dioxocyclohexanecarboxylate, dissolved in 100 ml dichloromethane and 15 ml triethylamine, at 10° C. The mixture was stirred for 3 hours at room temperature, poured into ice, separated, the organic phase shaken with 1N hydrochloric acid, saturated sodium bicarbonate and water, dried (magnesium sulphate) and concentrated. The ethyl 3-benzoyloxy-5-oxo-3-cyclohexenecarboxylate, so obtained, was dissolved in 75 ml acetonitrile and after addition of 15 ml triethylamine and 1.5 ml 2-hydroxyisobutyronitrile, was stirred at 24 hours at room temperature. The mixture was taken up in 100 ml diethyl ether and extracted with 100 ml 2N hydrochloric acid and then twice with, each time, 50 ml 5% potassium carbonate solution. After covering the aqueous phase with a layer of 100 ml diethyl ether, it was acidified with 4N hydrochloric acid until it was pH 3, separated, washed with water, dried (magnesium sulphate) and evaporated on a rotary evaporator. It was purified by recrystallising from hexane.

Workup

  1. customat 10° C
  2. additionpoured into ice
  3. customseparated
  4. stirringthe organic phase shaken with 1N hydrochloric acid, saturated sodium bicarbonate and water
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af2675a4e17f4d40ba9df1a2ee9de649
Source dataset
uspto-grants-1990_07
Patent number
US04943310

Reaction notes

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